A Biomimetic Approach to the Synthesis of the Core Structure of the Marine Sponge Terpene Halichonadin G | Zendy

Saito Kenta | Zendy; Nishimori Ayumu | Zendy; Mimura Rika | Zendy; Nakano Keiji | Zendy; Kotsuki Hiyoshizo | Zendy; Masuda Toshiya | Zendy; Ichikawa Yoshiyasu | Zendy

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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.

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