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Bioscience, Biotechnology, and Biochemistry Volume 70, 2006 - Issue 12
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Original Articles

Syntheses of Naturally Occurring Terphenyls and Related Compounds

Yusuke SAWAYAMAGraduate School of Bioagricultural Sciences, Nagoya University
,
Takashi TSUJIMOTOPRESTO of Japan Science and Technology Agency (JST)
,
Kumi SUGINOGraduate School of Bioagricultural Sciences, Nagoya University
,
Toshio NISHIKAWAGraduate School of Bioagricultural Sciences, Nagoya University;PRESTO of Japan Science and Technology Agency (JST)
,
Minoru ISOBEGraduate School of Bioagricultural Sciences, Nagoya University
&
Hirokazu KAWAGISHIGraduate School of Science and Technology, Shizuoka University
Pages 2998-3003 | Received 10 Jul 2006, Accepted 04 Aug 2006, Published online: 22 May 2014

  • 1) Gill, M., and Steglich, W., Pigment of fungi (Macromycetes). Prog. Chem. Org. Nat. Prod., 51, 1–317 (1987).
  • 2) Liu, J.-K., Natural terphenyls: developments since 1877. Chem. Rev., 106, 2209–2223 (2006).
  • 3) Nakagawa, F., Enokita, R., Naito, A., Iijima, Y., and Yamazaki, M., Terferol, an inhibitor of cyclic adenosine 3′,5′-monophosphate phosphodiesterase. I. Isolation and characterization. J. Antibiotics, 37, 6–9 (1984).
  • 4) Nakagawa, F., Takahashi, S., Naito, A., Sato, S., Iwabuchi, S., and Tamura, C., Terferol, an inhibitor of cyclic adenosine 3′,5′-monophosphate phosphodiesterase. II. Structural elucidation. J. Antibiotics, 37, 10–12 (1984).
  • 5) Wanzlick, H.-W., and Jahnke, U., Synthese des xylerithrins. Chem. Ber., 101, 3753–3760 (1968).
  • 6) Zhang, C., Ondeyka, J. G., Herath, K. B., Guan, Z., Collado, J., Pelaez, F., Leavitt, P. S., Gurnett, A., Nare, B., Liberator, P., and Singh, S. B., Highly substituted terphenyls as inhibitors of parasite cGMP-dependent protein kinase activity. J. Nat. Prod., 69, 710–712 (2006).
  • 7) Sano, Y., Sayama, K., Arimoto, Y., Inakuma, T., Kobayashi, K., Koshino, H., and Kawagishi, H., Ustalic acid as a toxin and related compounds from the mushroom Tricholoma ustale. Chem. Commun., 1384–1385 (2002).
  • 8) McMorris, T. C., and Anchel, M., The structure of the basidiomycete ortho quinone, phlebiarubrone, and of its novel acetylation product. Tetrahedron, 23, 3985–3991 (1967).
  • 9) Gripenberg, J., Fungus pigment XVII. The synthesis of phlebiarubrone. Tetrahedron Lett., 697–698 (1966).
  • 10) Yamazoe, A., Hayashi, K., Kuboki, A., Ohira, S., and Nozaki, H., The isolation, structural determination, and total synthesis of terfestatin A, a novel auxin signaling inhibitor from Streptomyces sp. Tetrahedron Lett., 45, 8359–8362 (2004).
  • 11) Cain, B. F., Potential anti-tumor agents. Part 1. Polyporic acid series. J. Chem. Soc., 936–940 (1961).
  • 12) Balogh, V., Fetizon, M., and Golfier, M., Oxidation with silver carbonate/Celite. V. Oxidations of phenols and related compounds. J. Org. Chem., 36, 1339–1341 (1971).
  • 13) Teuber, H. J., Use of dipotassium nitrosodisulfonate (Fremy’s salt), 4,5-dimethyl-o-benzoquinone. Org. Synth. Coll., 6, 480–481 (1972).
  • 14) Jokela, R., and Lounasmaa, M., p-Terphenyl- and phenanthraquinone derivatives: an NMR study. Planta Med., 63, 381–383 (1997).
  • 15) Demmin, T. R., and Rogic, M. M., Preparation of muconic acid anhydrides. Characterization of the 1-oxacyclohepta-3,5-diene-2,7-dione structure. J. Org. Chem., 45, 1153–1156 (1980).
  • 16) Ando, W., Miyazaki, H., and Akasaka, T., Oxidative ring cleavage of o-benzoquinone by potassium peroxomonosulphate. J. Chem. Soc., Chem. Commun., 518–519 (1983).
  • 17) Moro-oka, Y., and Foote, C. S., Chemistry of superoxide ion. Oxidation of 3,5-di-tert-butylcatechol with KO2. J. Am. Chem. Soc., 98, 1510–1514 (1976).
  • 18) Tsuji, J., and Takayanagi, H., Organic synthesis by means of metal complexes. XIII. Efficient, non-enzymatic oxidation of catechol with molecular oxygen activated by cuprous chloride to cis,cis-muconoate as the model reaction for pyrocatechase. J. Am. Chem. Soc., 96, 7349–7350 (1974).
  • 19) Bucher, J. E., The constitution of retene and derivatives. J. Am. Chem. Soc., 32, 374–382 (1910).
  • 20) Byrne, L. A., and Gilheany, D. G., Simple syntheses of seven-membered rings via an entropy/strain reduction strategy. Synlett, 933–943 (2004).
  • 21) Matsuura, T., Marsushima, H., Kato, S., and Saito, I., Photo-induced reactions-LVII, photosensitized oxygenation of catechol and hydroquinone derivatives: nonenzymatic models for the enzymatic cleavage of phenolic rings. Tetrahedron, 28, 5119–5129 (1972).
  • 22) Hashimoto, N., Aoyama, T., and Shioiri, T., New methods and reagents in organic synthesis. 14. A simple efficient preparation of methyl esters with trimethylsilyldiazomethane (TMSCHN2) and its application to gas chromatographic analysis of fatty acid. Chem. Pharm. Bull., 29, 1475–1478 (1981).
  • 23) Hesse, M., Meier, H., and Zeeh, B., Spectroscopic Methods in Organic Chemistry, Georg Thieme Verlag Stuttgart, New York, p. 248 (1997).

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