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Paper | Regular issue | Vol 92, No. 6, 2016, pp.1040-1053
Published online, 18th April, 2016
DOI: 10.3987/COM-16-13442
A Biomimetic Approach to the Synthesis of Terpene-Amino Acid Conjugates. The Ugi Reaction in the Hypothetical Biosynthesis of Marine Natural Products

Yoshiyasu Ichikawa,* Kenta Saito, Rika Mimura, Ayumi Kitamori, Akihito Matsukawa, Akifumi Ikeda, Toshiya Masuda, Hiyoshizo Kotsuki, and Keiji Nakano

*Faculty of Science, Kochi University, 2-5-1, Akebono-cho, Kochi 780-8520, Japan

Abstract

A unique pathway for the biosynthesis of the marine sponge terpenes, exigurin and boneratamides A–C, is proposed. Based on this proposal, a biomimetic strategy on key Ugi coupling reactions between terpene isocyanides and amino acids was developed for construction of the core structures of exigurin and boneratamides A–C.