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J-GLOBAL ID：201602254458543984   Reference number：16A1175465

A BIOMIMETIC APPROACH TO THE SYNTHESIS OF TERPENE-AMINO ACID CONJUGATES. THE UGI REACTION IN THE HYPOTHETICAL BIOSYNTHESIS OF MARINE NATURAL PRODUCTS

テルペン-アミノ酸複合体の合成のための生体模倣経路 海洋天然物の仮想生合成におけるUgi反応

Author (9)： ICHIKAWA Yoshiyasu (Kochi Univ., Kochi, JPN) ,  SAITO Kenta (Kochi Univ., Kochi, JPN) ,  MIMURA Rika (Kochi Univ., Kochi, JPN) ,  KITAMORI Ayumi (Kochi Univ., Kochi, JPN) ,  MATSUKAWA Akihito (Kochi Univ., Kochi, JPN) ,  IKEDA Akifumi (Kochi Univ., Kochi, JPN) ,  MASUDA Toshiya (Osaka City Univ.) ,  KOTSUKI Hiyoshizo (Kochi Univ., Kochi, JPN) ,  NAKANO Keiji (Kochi Univ., Kochi, JPN)
Material： Heterocycles  (International Journal for Reviews and Communications in Heterocyclic Chemistry)
Volume： 92  Issue： 6  Page： 1040-1053  Publication year： Jun. 01, 2016 
JST Material Number： S0966A  ISSN： 0385-5414  CODEN： HTCYAM  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： aquatic product ,  chemical synthesis ,  *terpenoid ,  amino acid ,  condensation reaction ,  marine natural product
Semi thesaurus term： *Ugi reaction ,  Terpenes ,  *Biomimetic synthesis

JST classification (1)： Terpenoids in general  (CF10021J)

Substance index (6)： Exigurin ,  Boneratamide A ,  Boneratamide B ,  Boneratamide B methyl ester ,  1-[(R)-2-[(2β-Isopropyl-5α-methylcyclohexane-1β-yl)amino]-1-methyl-2-oxoethyl]-5-oxopyrrolidine-2α-carboxylic acid methyl ester ,  1-[(S)-2-[(2β-Isopropyl-5α-methylcyclohexane-1β-yl)amino]-1-methyl-2-oxoethyl]-5-oxopyrrolidine-2α-carboxylic acid methyl ester

Reference (15)：

• To the best of our knowledge, exigurin is the first literature-emerged example of secondary metabolites produced through the Ugi reaction. a) M. M. Uy, S. Ohta, M. Yanai, E. Ohta, T. Hirata, and S. Ikegami, Tetrahedron, 2003, 59, 731. For other natural products presumably derived from the Ugi reaction, see the references; b) E. Aviles and A. D. Rodriguez, Org. Lett., 2010, 12, 5290; c) S. Suto, N. Tanaka, J. Fromont, and J. Kobayashi, Tetrahedron Lett., 2011, 52, 3470; d) N. Tanaka, S. Suto, H. Ishiyama, T. Kubota, A. Yarnano, M. Shiro, J. Fromont, and J. Kobayashi, Org. Lett., 2012, 14, 3498; e) N. Tanaka, S. Suto, M. Asai, T. Kusama, A. Takahashi-Nakaguchi, T. Gonoi, J. Fromont, and J. Kobayashi, Heterocycles, 2015, 90, 173.
• T. Okino, E. Yoshimura, H. Hirota, and N. Fusetani, Tetrahedron, 1996, 52, 9447.
• M. J. Garson and J. S. Simpson, Nat. Prod. Rep., 2004, 21, 164.
• D. E. Williams, B. O. Patrick, A. Tahir, R. Van Soest, M. Roberge, and R. J. Andersen, J. Nat. Prod., 2004, 67, 1752.
• This work has been communicated in preliminary form. See the reference, K. Saito, A. Nishimori, H. Kotsuki, K. Nakano, and Y. Ichikawa, Synlett, 2013, 24, 757.

Terms in the title (9)： テルペン ,  アミノ酸 ,  複合体 ,  生体模倣 ,  経路 ,  海洋天然物 ,  仮想 ,  生合成 ,  Ugi反応