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A Biomimetic Approach to the Synthesis of the Core Structure of the Marine Sponge Terpene Halichonadin G
Author(s) -
Saito Kenta,
Nishimori Ayumu,
Mimura Rika,
Nakano Keiji,
Kotsuki Hiyoshizo,
Masuda Toshiya,
Ichikawa Yoshiyasu
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301206
Subject(s) - sponge , chemistry , biomimetic synthesis , isocyanide , isocyanate , terpene , stereochemistry , combinatorial chemistry , organic chemistry , botany , polyurethane , biology
A pathway for the biosynthesis of halichonadin G involving the unique action of ugiase and isocyanide oxidase is proposed. This hypothesis was tested in a biomimetic approach to the synthesis of the core structural unit of this marine sponge terpene, which relies on a key Ugi coupling reaction and an isocyanide‐to‐isocyanate oxidative transformation. The results of this effort demonstrate that the biomimetic strategy can be employed to construct the core structure of halichonadin G in an efficient manner.