KINDAI UNIVERSITY


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YAMAGIWA Yoshiro

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FacultyDepartment of Science / Graduate School of Science and Engineering Research
PositionAssociate Professor
Degree
Commentator Guidehttps://www.kindai.ac.jp/meikan/361-yamagiwa-yoshirou.html
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Last Updated :2020/04/08

Education and Career

Education

  •  - 1983 , Osaka City University
  •  - 1983 , Osaka City University, Graduate School, Division of Natural Science
  •  - 1981 , Osaka City University, Faculty of Science
  •  - 1981 , Osaka City University, Faculty of Science

Research Activities

Research Areas

  • Life sciences, Bioorganic chemistry
  • Nanotechnology/Materials, Structural/physical organic chemistry

Published Papers

  • Inhibitory effects of cardols and related compounds on superoxide anion generation by xanthine oxidase, Masuoka Noriyoshi, Nihei Ken-ichi, Maeta Ayami, Yamagiwa Yoshiro, Kubo Isao, FOOD CHEMISTRY, FOOD CHEMISTRY, 166, 270 - 274, Jan. 01 2015 , Refereed
  • 2-hydroxy-4-isopropylbenzaldehyde, a potent partial tyrosinase inhibitor., Nihei K, Yamagiwa Y, Kamikawa T, Kubo I, Bioorganic & medicinal chemistry letters, Bioorganic & medicinal chemistry letters, 14(3), 681 - 683, Feb. 2004 , Refereed
  • Molecular design of antifungal agents., Kubo I, Xiao P, Nihei K, Fujita K, Yamagiwa Y, Kamikawa T, Journal of agricultural and food chemistry, Journal of agricultural and food chemistry, 50(14), 3992 - 3998, Jul. 2002 , Refereed
  • Molecular Design of Antibrowning Agents (共著), Isao Kubo, Ikuyo Kinst-Hori, Yumi Kubo, Yoshiro Yamagiwa, Tadao Kamikawa, Hiroyuki Haraguchi, J. Agric. Food Chem., J. Agric. Food Chem., 48(4), 1393 - 1399, May 17 2000
    Summary:Tyrosinase inhibitory and antioxidant activity of gallic acid and its series of alkyl chain esters were investigated. All inhibited the oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA) catalyzed by mushroom tyrosinase. However, gallic acid and its short alkyl chain esters were oxidized as substrates yielding the colored oxidation products. In contrast, the long alkyl chain esters inhibited the enzyme activity without being oxidized. This indicates that the carbon chain length is associated with their tyrosinase inhibitory activity, presumably by interacting with the hydrophobic protein pocket in the enzyme. On the other hand, the esters, regardless their carbon chain length, showed potent scavenging activity on the autoxidation of linoleic acid and 1,1-diphenyl-2-p-picryhydrazyl (DPPH) radical, suggesting that the alkyl chain length is not related to the activity. The effects of side-chain length of gallates in relation to their antibrowning activity are studied.
  • A New Route to Phenazines (共著), Takahiro Emoto, Nobuo Kubosaki, Yoshiro Yamagiwa, Tadao Kamikawa, Tetrahedron Lett, Tetrahedron Lett, 41(3), 355 - 358, Jan. 15 2000
    Summary:Phenazines were prepared by the palladium(II)-catalyzed intramolecular amination of aryl bromides 8, which were prepared with o-bromonitrobenzenes 3 and anilines 4 or 3 and o-bromoanilines 5 using palladium(II)catalyzed aniline arylation.
  • Unique tetranuclear copper(II) cluster and monomeric iron(II), (III) complexes with a tris(imidazolyl) chelating ligand, Liang Ping Wu, Yoshiro Yamagiwa, Ichirou Ino, Kunihisa Sugimoto, Takayoshi Kuroda-Sowa, Tadao Kamikawa, Megumu Munakata, Polyhedron, Polyhedron, 18, 2047 - 2053, Jun. 11 1999
    Summary:Copper(II) and iron(II, III) complexes of the tripodal ligand, tris(1-methyl-1H-imidazol-2-yl)methanol (Htmim), have been synthesized and characterized by elemental analysis, 1 H NMR and IR spectroscopies, magnetic moment measurement and X-ray crystallography. The structure of the copper complex, [Cu 4 (tmim) 4 (CF 3 SO 3 ) 2 ](CF 3 SO 3 ) 2 ·2MeOH (1), can be regarded as a polyimidazole-linked tetranuclear cluster where each copper atom adopts a five-coordinate square-pyramidal geometry ligated by the tmim anion. The two iron complexes, [Fe II (Htmim) 2 ][Fe II Cl 4 ]·4MeOH (2) and [Fe III (Htmim) 2 ][Fe III Cl 4 ] 2 Cl (3), contain the isostructural [Fe(Htmim) 2 ] cation and tetrahedral [FeCl 4 ] - anion. While Htmim shows a normal tripodal tridentate mode in the iron complexes capping one face of an essentially octahedral coordination sphere, its deprotonated species exhibit an unusual non-tripodal tetradentate coordination with copper(II) ions. The observed magnetic moment at room temperature for 1 is 1.13 BM per Cu atom, consistent with antiferromagnetic coupling between the copper(II) atoms of the tetramer. Both 2 and 3 show magnetic properties consistent with low-spin electronic configurations of the cation and high-spin nature of the metal ion in the anion. © Elsevier Science Ltd.
  • Synthesis and structure of a three-dimensional copper(II) coordination polymer with 1,2-bis(imidazol-1′-yl)ethane, Liang Ping Wu, Yoshiro Yamagiwa, Takayoshi Kuroda-Sowa, Tadao Kamikawa, Megumu Munakata, Inorganica Chimica Acta, Inorganica Chimica Acta, 256, 155 - 159, Mar. 15 1997
    Summary:The synthesis and characterization of the copper(II) complex [Cu(bim) 2.5 ](ClO 4 ) 2 ·2MeOH, where bim=1,2-bis(imidazol-1′-yl)ethane, is described. The complex crystallizes in the monoclinic system, space group P2 1 /a, with cell constants a=12.280(8), b=12.533(5), c=19.490(9) Å, β=92.17(5)° and Z=4. The structure was solved by a direct method and refined by full-matrix least-squares to a residual R value of 0.064 and R w of 0.066. The complex contains non-interacting ClO 4 - anions and a {[Cu(bim) 2.5 ] 2+ } ∞ macrocation in which each metal ion involves a distorted square-based pyramidal coordination environment comprising five N atoms from five separate bim molecules. The total structure consists of two alternately stacked 2D sheets of copper(II) ions bridged through the bidentate imidazole molecules constituting a three-dimensional network. Consistent with the observed structural data the complex shows a typical axially symmetric ESR signal at room temperature.
  • Synthesis of Imidazole-Containing Ligands and Studies on Metal Complexes, Yoshiro Yamagiwa, Yoshiro Koreishi, Satoshi Kiyozumi, Masanori Kobayashi, Tadao Kamikawa, Mitsuji Tsukino, Hironori Goi, Mikiko Yamamoto, Megumu Munakata, Bulletin of the Chemical Society of Japan, Bulletin of the Chemical Society of Japan, 69, 3317 - 3323, Nov. 01 1996
    Summary:1,5-Di(imidazol-l-yl)-3-(2-(imidazol-l-yl)ethyl]pentane, 1,7-di(imidazol-l-yl)-4-[3-(imidazol-l-yl)propyl] heptane, N,N′,N″ -tris[2-(imidazol-4-yl)ethyl]benzene-1,3,5-tricarboxamide, and 1,3,5-tris[3-(imidazol-l-yl)propyl] benzene (TIPB) have been synthesized for a study of the formation and characteristics of zinc complexes. TIPB forms a crystalline zinc complex, not a tetrahedral complex but an octahedral complex. Other ligands form either microcrystalline complexes or polymer complexes with zinc.
  • SRS-A antagonist pyranoquinolone alkaloids from East African Fagara plants and their synthesis(共著), Tadao Kamikawa, Yasuyuki Hanaoka, Satoru Fujie, Ken Saito, Yoshiro Yamagiwa, Katsuya Fukuhara, Isao Kubo, Bioorganic Med. Chem. ,, Bioorganic Med. Chem. ,, 4(8), 1317 - 1320, Aug. 01 1996
    Summary:Three pyranoquinolone alkaloids isolated from two East African Fagara plants have been found to exhibit SRS-A antagonist action. Their synthesis has been accomplished, using a modified Coppola's method or a thermal cyclization followed by an electrocyclic ring closure.
  • Synthesis of a straight chain analog of penaresidins, azetidine alkaloids from marine sponge Penares sp., Tadaaki Hiraki, Yoshiro Yamagiwa, Tadao Kamikawa, Tetrahedron Letters, Tetrahedron Letters, 36, 4841 - 4844, Jul. 03 1995
    Summary:The straight-chain analog of penaresidins, azetidine alkaloids from the Okinawan marine sponge Penares sp., have been synthesized from D-xylose. The key step in the synthesis includes the biomimetic-type ring closure of phytosphingosines. The novel isomerization through an azabicylobutyl ion-pair is also described. © 1995.
  • Total synthesis of (2S,3S,4R)-2-[(2′R)-2-benzoyloxydocosanoylamino]-16-methylheptadecane-1,3,4,-triol 3,4-dibenzoate, a partially protected ceramide part of sponge cerebrosides, Hideki Nakashima, Norihiko Hirata, Takeru Iwamura, Yoshiro Yamagiwa, Tadao Kamikawa, Journal of the Chemical Society, Perkin Transactions 1, Journal of the Chemical Society, Perkin Transactions 1, 2849 - 2857, Jan. 01 1994
    Summary:(2S,3S,4R)-2-[(2′R)-2-Benzoyloxydocosanoylamino]-16-methylheptadecane-1,3,4-triol 3,4-dibenzoate 32, a partially protected ceramide part of a cerebroside from the marine sponge Halichondria japonica, has been synthesized from L-ascorbic acid, and its absolute stereochemistry has been determined. The key steps in the synthesis include the regioselective ring opening of chiral epoxide 5 with a 2-alkyl-2-lithio-1,3-dithiane and the introduction of a hydroxymethylene synthon using Dondoni's protocol to assemble C(1) and C(2) functionality. © 1994 by the Royal Society of Chemistry. All Rights Reserved.
  • Synthesis of 2,3-di-O-phytanyl-1-O-(α-D-glucopyranosyl)-sn-glycerol derivatives, analogues of polar lipids isolated from a halophilic bacterial strain, Tadao Kamikawa, Koji Nogawa, Yoshiro Yamagiwa, Glycoconjugate Journal, Glycoconjugate Journal, 10, 235 - 239, Jun. 01 1993
    Summary:2,3-Di-O-phytanyl-1-O-glucopyranosylglycerol and polar derivatives of its 6′-glucose moiety have been synthesized. The target molecule contains the diphytanyl-sn-glycerol moiety which is α-linked to glucose. The key step in its synthesis involves the coupling of phytanyl bromide and isopropylidene threitol. We also demonstrated that the 6′-hydroxyl group of glycolipids can be functionalized without protection of the sugar moiety. © 1993 Chapman & Hall.
  • Structure-Antibacterial Activity Relationships of Anacardic Acids (共著), Isao Kubo, Hisae Muroi, Masaki Himejima, Yoshiro Yamagiwa, Hiroyuki Mera, Kimihiro Tokushima, Shigeo Ohta, Tadao Kamikawa, J. Agric. Food Chem., J. Agric. Food Chem., 41(6), 1016 - 1019, Jan. 01 1993
    Summary:A series of anacardic acids possessing different side-chain lengths were synthesized, and their antimicrobial activity was tested. In the case against Staphylococcus aureus, the anacardic acid having the C 10 alkyl side chain was most active, while against Propionibacterium acnes, Streptococcus mutans, and Brevibacterium ammoniagenes, the anacardic acid possessing the C 12 alkyl side chain was most effective. © 1993, American Chemical Society. All rights reserved.
  • A convenient stereoselective synthesis of D-erythro-C<inf>18</inf>-sphingosine from galactal, Norihiko Hirata, Yoshiro Yamagiwa, Tadao Kamikawa, Journal of the Chemical Society, Perkin Transactions 1, Journal of the Chemical Society, Perkin Transactions 1, 2279 - 2280, Jan. 01 1991
    Summary:The highly efficient stereoselective synthesis of D-erythro-C < inf > 18 < /inf > -sphingosine from 3,4,6-tribenzyl- oxygalactal via 4,6-tribenzyloxy-5-hydroxyhexenal is described. © 1991 by the Royal Society of Chemistry.
  • Effect of a marine algal constituent on the growth of lettuce and rice seedings(共著), Isao Kubo, Masamitsu Ochi, Kozo Shibata, Frederick J. Hanke, Tetsuo Nakatsu, Kah Siew Tan, Makoto Taniguchi, Tadao Kamikawa, Yoshiro Yamagiwa, Mitsuo Arizuka, William F. Wood, J. Nat. Prod., J. Nat. Prod., 53(1), 50 - 56, Jan. 01 1990
    Summary:The dibromocatechol α-O-methyllanosol [1], a methyl ether of lanosol, was isolated from both the MeOH and the CH 2 C1 2 extracts of Odonthalia washingtoniensis and Odonthalia floccosa. Its structure was confirmed through spectroscopic methods and through its synthesis. An investigation of its biological activities revealed that it exhibits a stimulating effect on the growth and elongation of certain terrestrial plants both in the in vivo and the in vitro systems. © 1990, American Chemical Society. All rights reserved.
  • Isolation, structure, and synthesis of noel 4-quinolinone alkaloids from esenbeckia leiocarpa, Tetsuo Nakatsu, Timothy Johns, Isao Kubo, Katharine Milton, Masami Sakai, Katsuhiro Chatani, Ken Satto, Yoshiro Yamagiwa, Tadao Kamikawa, Journal of Natural Products, Journal of Natural Products, 53, 1508 - 1513, Jan. 01 1990
    Summary:Two new biocidal quinolinone alkaloids, 3-methoxy-1-methyl-2-propyl-4-quinolone [1] and 2(1ʹ-ethylpropyl)-1-methyl-4-quinolone [2] , were efficiently isolated using reversed-phase recycling hplc from the leaves of Esenbeckia leiocarpa. The structures were determined through spectroscopic data and confirmed by total synthesis. These alkaloids have antifeedant activities against the pink boll worm, Pectinophora gossypiella. © 1990, American Chemical Society. All rights reserved.
  • Synthesis of chiral long-chain α-hydroxy acids from L-ascorbic acid. Useful components for the synthesis of cerebrosides, Kazuyuki Yamagata, Yoshiro Yamagiwa, Tadao Kamikawa, Journal of the Chemical Society, Perkin Transactions 1, Journal of the Chemical Society, Perkin Transactions 1, 3355 - 3357, Jan. 01 1990
    Summary:Nucleophilic ring opening of chiral epoxy diols, derived from L-ascorbic acid, with 2-lithio-1,3-dithianes allowed preparation of long-chain (R)- and (S)-α-hydroxy acids of high optical purity. © 1990 by The Royal Society of Chemistry.
  • Synthesis of cis- and trans-15,16-epoxycleroda-13(16),14-dien-3-ones: Incompatibility with the structure of cascarillone, Hideo Iio, Kaoru Fujimori, Yoshiro Yamagiwa, Mitsugu Monden, Takashi Tokoroyama, Journal of the Chemical Society, Perkin Transactions 1, Journal of the Chemical Society, Perkin Transactions 1, 1359 - 1360, Dec. 01 1989
    Summary:The title cis- and trans-clerodanes the structures of which correspond to that proposed for cascarillone have been efficiently synthesized from previously reported intermediates; neither proved to be identical with cascarillone.
  • Synthesis of D-erythro-1-deoxydihydroceramide-1-sulfonic acid and phosphonosphingoglycolipid found in marine organisms via a common precursor(共著), Kinji Ohashi, Shunji Kosai, Mitsuo Arizuka, Takashi Watanabe, Yoshiro Yamagiwa, Tadao Kamikawa, Morris Kates, Tetrahedron, Tetrahedron, 45(9), 2557 - 2570, Jan. 01 1989
    Summary:D-Erythro-1-deoxydihydroceramide-1-sulfonic acid, isolated from alkali-stable hydrogenated lipids in a non-photosynthetic marine diatom, Nitzschia alba, and (2S,3R)-N-palmitoyl-1-O-[6'-O-2-(N-methylamino)ethylphosphonyl-β-D-galacto-pyranosyl]-D-sphingosine, found in marine snail Turbo cornutus were synthesized via a common precursor (10) starting from galactose. © 1989.
  • Synthesis of phosphonosphingoglycolipid found in marine snail turbo cornutus, Kinji Ohashi, Shunji Kosai, Mitsuo Arizuka, Takashi Watanabe, Mikio Fukunaga, Koji Monden, Takao Uchikoda, Yoshiro Yamagiwa, Tadao Kamikawa, Tetrahedron Letters, Tetrahedron Letters, 29, 1189 - 1192, Jan. 01 1988
    Summary:The phosphonosphingoglycolipid (1) found in marine snail Turbo cornutus is synthesized from galactose as a chiral precursor via condensation of cerebroside (7) with protected phosphonic acid using DEC as the key step. © 1988.
  • Synthesis of clitocine, a new insecticidal nucleoside from the mushroom Clitocybe inversa, Tadao Kamikawa, Satoru Fujie, Yoshiro Yamagiwa, Mujo Kim, Hitoshi Kawaguchi, Journal of the Chemical Society, Chemical Communications, Journal of the Chemical Society, Chemical Communications, 195 - 196, Jan. 01 1988
    Summary:Clitocine, a new insecticidal nucleoside from the mushroom Clitocybe inversa, was synthesized.
  • A general method for the synthesis of clerodane diterpenoids. Stereospecific total syntheses of (±)-15, 16-epoxy-cis-cleroda-3, 13(16), 14-triene and..., Takashi Tokoroyama, Kaoru Fujimori, Takayoshi Shimizu, Yoshiro Yamagiwa, Mitsugu Monden, Hideo Iio, Tetrahedron, Tetrahedron, 44, 6607 - 6622, Jan. 01 1988
    Summary:Title full: A general method for the synthesis of clerodane diterpenoids. Stereospecific total syntheses of (±)-15, 16-epoxy-cis-cleroda-3, 13(16), 14-triene and (±)-maingayic acid 1 1 Part 22 in Synthetic Studies on Terpenic Compounds. For Part 21 see: A. Kondo, T. Ochi, H. Iio, T. Tokoroyama and M. Siro, Chemistry Lett., 1987, 1491. Ref. 2 counts as Part 18. 2 2 A preliminary report of this work has been published: T. Tokoroyama, K. Fujimori, T. Shimizu, Y. Yamagiwa and H. Iio, J. Chem. Soc., Chem. Commun., 1983, 1516. A general method for the syntheses of cis- and trans-clerodane diterpenoids has been developed and its applications to the total syntheses of both representatives 11 and maingayic acid (32) in racemic forms are described. The common Δ 4 -3-octalone intermediates 2a and 2b were prepared from 3,4-dimethyl-2-cyclohexenone by a stereospecific conjugate addition-alkylation sequence and the subsequent thermodynamically controlled annelation. The dimethylcuprate addition to 2a followed by enolate trapping afforded stereospecifically the cis-alcohol 12, from which (±)-11 has been synthesized. On the other hand hydrocyanation of 2b gave trans-intermediate 33, and then it has been converted to (±)-maingayic acid (32). © 1988.
  • Syntheses of anacardic acids and ginkgoic acid(共著), Yoshiro Yamagiwa, Kinji Ohashi, Yoshitaka Sakamota, Shinji Hirakawa, Tadao Kamikawa, Isao Kubo, Tetrahedron, Tetrahedron, 43(15), 3387 - 3394, Jan. 01 1987
    Summary:Syntheses of two anacardic acids [6-pentadecyl- and 6-(10-pentadecenyl) salicylic acid], inhibitors of prostaglandin synthetase and of the growth of certain insects, and ginkgoic acid via directive metallation is reported. © 1987.
  • Synthesis of 3-(ω-phenylalkyl)catechols, phenolic lipids found in sap of the burmese lac tree, via directed metallation, Yoshiaki Furukawa, Yoshiro Yamagiwa, Tadao Kamikawa, Journal of the Chemical Society - Series Chemical Communications, Journal of the Chemical Society - Series Chemical Communications, 1234 - 1235, Jan. 01 1986
    Summary:3-(ω-Phenylalkyl)catechols were synthesized via directed metallation. © Royal Society of Chemistry.
  • Synthesis of hepialone; principal component from male sex scales of hepialus californicus (lepidoptera), Keiso Uchino, Yoshiro Yamagiwa, Tadao Kamikawa, Isao Kubo, Tetrahedron Letters, Tetrahedron Letters, 26, 1319 - 1320, Jan. 01 1985
    Summary:Racemic and optically active hepialone, a new sex-pheromonal component produced by the male moth, Hepialus californicus Bvd., was synthesized and thus confirmed the structure of the pheromone as (2R)-2,3-dihydro-2-ethyl-6-methyl-4H-pyran-4-one (1). © 1985.
  • A versatile method for the synthesis of clerodane diterpenoids: Syntheses of cis and trans representatives, Takashi Tokoroyama, Kaoru Fujimori, Takayoshi Shimizu, Yoshiro Yamagiwa, Mitsugu Monden, Hideo Iio, Journal of the Chemical Society, Chemical Communications, Journal of the Chemical Society, Chemical Communications, 1516 - 1518, Dec. 01 1983
    Summary:Application of stereospecific conjugate addition reactions to Δ 4 -3-octalone intermediates has led to the total synthesis of both cis- and trans-clerodane diterpenes.

Conference Activities & Talks

  • (2PB-61)Synthetic studies of Cytonic Acids A and B, YAMASHITA Taiki, YAMAGIWA Yoshiro, NAKAGAWA Takayo,   2017 03 17
  • (3PB-223)Synthetic study of Integrastatins, KAWAKAMI Hideki, SHIGEKAWA Yoya, YAMAGIWA Yoshiro,   2016 03 26
  • (3PB-222)Total Synthesis of Integracins A and B, Fujita Atsushi, TAKAYAMA Yoshiko, MAEKAWA Takehiko, YAMAGIWA Yoshiro,   2016 03 26
  • Synthetic study on Benthocyanin A, a potent radical scavenger, 岡島史典, 樋口琢磨, 山際由朗, 日本化学会講演予稿集,   2010 03 12
  • 北米産のカンゾウの抗HIV成分Glepidotin Dの全合成, 山際由朗, 原孝徳, 矢田幸昌, 左近直樹, 日本化学会講演予稿集,   2007 03 12
  • Synthetic study of Poryketide L-755,805, 山際由朗, 寺田勇介, 日本化学会講演予稿集,   2006 03 13
  • Synthetic study of Euplexide C, 菱田智之, 山際由朗, 日本化学会講演予稿集,   2004 03 11
  • Synthetic Study of Bioactive p.Terphenyls, 片岡慎太郎, 山田健, 山際由朗, 神川忠雄, 日本化学会講演予稿集,   2003 03 03
  • Synthesis of Parvisporin, a novel neuritogenic compound, 中野恵望子, 佐々木幹子, 榎本聡, 山際由朗, 神川忠雄, 日本化学会講演予稿集,   2002 03 11
  • Total synthesis of neuronal cell protecting substance Phenazostatin A, 酒井康行, 山際由朗, 神川忠雄, 日本化学会講演予稿集,   2001 03 15
  • Syntheses of polyprenyl hydroquinones via coupling reaction of allyl mesylate and arylzinc compound, 榎本聡, 小林豊茂, 山際由朗, 神川忠雄, 日本化学会講演予稿集,   2001 03 15
  • A new route to phenazines., 神川忠雄, 山際由朗, 榎本貴弘, 窪崎伸夫, 天然有機化合物討論会講演要旨集,   2000 10 01
  • 117(P-50) A new route to phenazines, Kamikawa Tadao, Yamagiwa Yoshiro, Emoto Takahiro, Kubosaki Nobuo, 天然有機化合物討論会講演要旨集,   2000 10 01
    Summary:Naturally occurring phenazines have attracted considerable attention because of their interesting biological activities. One of the most promising methods for synthesizing polysubstituted phenazines developed by Holliman and co-workers was the reductive cyclization of o-nitrodiphenylamines (Method C). However, the yield was poor when competitive cyclization occurred. Recently, N-arylation has become more accessible owing to the advent of a new methodology developed by Hartwig and Buchwald. Here, we report on the use of the new method to synthesize phenazines using sequential palladium-mediated aniline arylation. Our method is based on the regiospecific bromination of o-nitrodiphenylamine 3, which is obtained from o-bromonitrobenzene 1 and aniline 2 by aniline arylation, to give bromide 4 (Method A), which is also obtained from 1 and o-bromoaniline 5 (Method B). Subsequent chemoselective reduction of the nitro group on 4 followed by the Hartwig-Buchwald aniline arylation affords the target phenazine. For the total synthesis of benthocyanin A, a powerful radical scavenger from the mycelium of Streptomyces prunicolor, and of phenazostatin A, a new neuronal cell protecting substances from the culture broth of Streptomyces sp. 833, we adapted the new methods to construct phenazines.
  • 117(P-50) A new route to phenazines, Kamikawa Tadao, Yamagiwa Yoshiro, Emoto Takahiro, Kubosaki Nobuo, Symposium on the Chemistry of Natural Products, symposium papers,   2000
    Summary:Naturally occurring phenazines have attracted considerable attention because of their interesting biological activities. One of the most promising methods for synthesizing polysubstituted phenazines developed by Holliman and co-workers was the reductive cyclization of o-nitrodiphenylamines (Method C). However, the yield was poor when competitive cyclization occurred. Recently, N-arylation has become more accessible owing to the advent of a new methodology developed by Hartwig and Buchwald. Here, we report on the use of the new method to synthesize phenazines using sequential palladium-mediated aniline arylation. Our method is based on the regiospecific bromination of o-nitrodiphenylamine 3, which is obtained from o-bromonitrobenzene 1 and aniline 2 by aniline arylation, to give bromide 4 (Method A), which is also obtained from 1 and o-bromoaniline 5 (Method B). Subsequent chemoselective reduction of the nitro group on 4 followed by the Hartwig-Buchwald aniline arylation affords the target phenazine. For the total synthesis of benthocyanin A, a powerful radical scavenger from the mycelium of Streptomyces prunicolor, and of phenazostatin A, a new neuronal cell protecting substances from the culture broth of Streptomyces sp. 833, we adapted the new methods to construct phenazines.
  • P-48 SYNTHETIC STUDIES ON BIOACTIVE LIPIDS DERIVED FROM PHYTOSPHINGOSINE, Nakashima H, Hiraki T, Yamagiwa Y, Kamikawa T, 天然有機化合物討論会講演要旨集,   1994 09 20
    Summary:We have studied the syntheses of bioactive lipids using natural chiral sources as starting materials. Hayashi et al. isolated a new ceramide digalactoside 1 as a main glycosphingolipid from the marine sponge Halichondria japonica. Penaresidin A 2 and B 3 were isolated as potent actomyosin ATPase activators from Okinawan marine sponge Penares sp. by Kobayashi et al. Here we describe synthetic studies of the ceramide part of I and the straight chain analog of 2. Synthesis of the ceramide part of 1. A partially protected ceramide part 20 of cerebroside 1 has been synthesized from L-ascorbic acid, and its absolute stereochemistry has been determined. The key step in the synthesis include the regioselective ring opening of chiral epoxide 7 with 2-alkyl-2-lithio-1,3-dithiane and the introduction of hydroxymethylene synthon using Dondoni's protocol to assemble C(1) and C(2) functionality. Synthesis of the straight chain analog of 2. The strategy for the construction of azetidine skeleton was a biogenetic-like intramolecular cyclization of a phytosphingosine analog 26, which, in turn, derived from xylose.
  • P-48 SYNTHETIC STUDIES ON BIOACTIVE LIPIDS DERIVED FROM PHYTOSPHINGOSINE, Nakashima H, Hiraki T, Yamagiwa Y, Kamikawa T, Symposium on the Chemistry of Natural Products, symposium papers,   1994
    Summary:We have studied the syntheses of bioactive lipids using natural chiral sources as starting materials. Hayashi et al. isolated a new ceramide digalactoside 1 as a main glycosphingolipid from the marine sponge Halichondria japonica. Penaresidin A 2 and B 3 were isolated as potent actomyosin ATPase activators from Okinawan marine sponge Penares sp. by Kobayashi et al. Here we describe synthetic studies of the ceramide part of I and the straight chain analog of 2. Synthesis of the ceramide part of 1. A partially protected ceramide part 20 of cerebroside 1 has been synthesized from L-ascorbic acid, and its absolute stereochemistry has been determined. The key step in the synthesis include the regioselective ring opening of chiral epoxide 7 with 2-alkyl-2-lithio-1,3-dithiane and the introduction of hydroxymethylene synthon using Dondoni's protocol to assemble C(1) and C(2) functionality. Synthesis of the straight chain analog of 2. The strategy for the construction of azetidine skeleton was a biogenetic-like intramolecular cyclization of a phytosphingosine analog 26, which, in turn, derived from xylose.
  • 47 SYNTHETIC STUDIES ON CLERODANE DITERPENOIDS, Tokoroyama T, Shimizu T, Yamagiwa Y, Monden M, Iio H, 天然有機化合物討論会講演要旨集,   1983 09 15
    Summary:In a continuation of our synthetic studies on clerodane diterpenoids, we have developed a general and versatile method for their syntheses. Its utility is demonstrated by the total syntheses of both cis and trans clerodane diterpenes, and by the contribution to the structure of cascarillone, a constituent of Cascarille oil. 1. Basic Strategy. The basic strategy rests on the conjugate addition of one carbon synthons to Δ^4-octal-3-one derivatives 2, which would afford cis or trans clerodane skeleton by appropriate choice of the reagents and conditions. (Scheme 1) 2. Synthesis of 15,16-Epoxy-cis-cleroda-3,13(16),14-triene 5. Conjugate addition of Me_2CuLi to octalone derivative 2a followed by trapping of the resulting enolate with HCHO gave a hydroxyketone 6, which was converted to the title natural product 5 by seven steps. (Scheme 2) 3. Syntheses of Maingayic Acid 19 and Annonene 20. Hydrocyanation of octalone intermediate 2b with Et_2AlCN gave stereospecifically a trans product 21, from which the total synthesis of maingayic acid, a piscicidal plant constituent, was accomplished by eleven steps via an aldehyde 33. Since 33 has been converted to annonene 20, our work constitutes also the formal synthesis of 20. (Scheme 3) 4. Structure Studies of Cascarillone. A cis-clerodane structure 34 was assigned to cascarillone solely on the basis of spectroscopic speculation. Our synthetic product 41 prepared starting from 7 has turned out to be not identical with cascarillone. Therefore the trans structure 42 is more likely for it and the confirmation of this proposal by synthesis is on progress.
  • 47 SYNTHETIC STUDIES ON CLERODANE DITERPENOIDS, Tokoroyama T, Shimizu T, Yamagiwa Y, Monden M, Iio H, Symposium on the Chemistry of Natural Products, symposium papers,   1983
    Summary:In a continuation of our synthetic studies on clerodane diterpenoids, we have developed a general and versatile method for their syntheses. Its utility is demonstrated by the total syntheses of both cis and trans clerodane diterpenes, and by the contribution to the structure of cascarillone, a constituent of Cascarille oil. 1. Basic Strategy. The basic strategy rests on the conjugate addition of one carbon synthons to Δ^4-octal-3-one derivatives 2, which would afford cis or trans clerodane skeleton by appropriate choice of the reagents and conditions. (Scheme 1) 2. Synthesis of 15,16-Epoxy-cis-cleroda-3,13(16),14-triene 5. Conjugate addition of Me_2CuLi to octalone derivative 2a followed by trapping of the resulting enolate with HCHO gave a hydroxyketone 6, which was converted to the title natural product 5 by seven steps. (Scheme 2) 3. Syntheses of Maingayic Acid 19 and Annonene 20. Hydrocyanation of octalone intermediate 2b with Et_2AlCN gave stereospecifically a trans product 21, from which the total synthesis of maingayic acid, a piscicidal plant constituent, was accomplished by eleven steps via an aldehyde 33. Since 33 has been converted to annonene 20, our work constitutes also the formal synthesis of 20. (Scheme 3) 4. Structure Studies of Cascarillone. A cis-clerodane structure 34 was assigned to cascarillone solely on the basis of spectroscopic speculation. Our synthetic product 41 prepared starting from 7 has turned out to be not identical with cascarillone. Therefore the trans structure 42 is more likely for it and the confirmation of this proposal by synthesis is on progress.

Misc

  • キサンチンオキシダーゼが触媒するスーパーオキシド生成反応のカルドールによる阻害, 益岡典芳, 金口裕生, 二瓶賢一, 山際由朗, 久保伊佐夫, 日本生化学会大会(Web), 87th, 2T16P-14(2P-178) (WEB ONLY), 14],   2014 10 , http://jglobal.jst.go.jp/public/201502297706679628
  • Synthesis of Model Compound to Mimic the Zinc Binding Site of Carbonic Anhydrase, Kamikawa Tadao, Yamagiwa Yoshiro, Kitamura Yoshiki, Report of the Environmental Science Research Institute, Kinki University, 19, 271, 275,   1991 10 , http://ci.nii.ac.jp/naid/110000508534
  • Synthetic Studies on Analogs of Clitocine, A New Nucleoside Insect Growth Inhibitor, Yamagiwa Yoshiro, Fujie Satoru, Makihara Koichi, Journal of the Faculty of Science and Technology, Kinki University, 24, 85, 91,   1988 09 , http://ci.nii.ac.jp/naid/110000173450
  • Synthetic of a Mosquito Oviposition Attractant Pheromone, Kamikawa Tadao, Yamagiwa Yoshiro, Katui Takakazu, Journal of the Faculty of Science and Technology, Kinki University, 23, 79, 84,   1987 09 , http://ci.nii.ac.jp/naid/110000173396
  • The Synthesis of N-Methylflindersine, an Insect Growth Inhibitor Isolated from African Medicinal Plants, Yamagiwa Yoshiro, Hanaoka Yasuyuki, Fujie Satoru, Journal of the Faculty of Science and Technology, Kinki University, 22, 99, 103,   1986 09 , http://ci.nii.ac.jp/naid/110000173344
  • Synthesis of N-Isobutyl 9-(p-Phenoxyphenyl)-2E,4E-nonadienamide. An Attempt at the Synthesis of Potent Insecticides, Kamikawa Tadao, Yamagiwa Yoshiro, Tanigami Shigeki, Journal of the Faculty of Science and Technology, Kinki University, 21, 105, 110,   1985 09 , http://ci.nii.ac.jp/naid/110000173292
  • Synthesis of N-Isobutyl 10-Phenoxy-2,4-decadienamide, Kamikawa Tadao, Yamagiwa Yoshiro, Ohta Masaaki, Journal of the Faculty of Science and Technology, Kinki University, 20, 127, 131,   1984 09 , http://ci.nii.ac.jp/naid/110000173224