Convergent Synthesis of the HIJKLMN-Ring Fragment of Caribbean Ciguatoxin C-CTX-1 by a Late-Stage Reductive Olefin Coupling Approach

Abstract The convergent synthesis of the HIJKLMN-ring fragment of Caribbean ciguatoxin C-CTX-1, the major causative toxin for ciguatera fish poisoning in the Caribbean Sea and the Northeast Atlantic areas, is disclosed. The synthesis features a late-stage iron-catalyzed hydrogen atom transfer-initia...

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Bibliographic Details
Published in:Bulletin of the Chemical Society of Japan
Main Authors: Sasaki, Makoto, Iwasaki, Kotaro, Arai, Keisuke, Hamada, Naoya, Umehara, Atsushi
Format: Article in Journal/Newspaper
Language:English
Published: Oxford University Press (OUP) 2022
Subjects:
General Chemistry
Northeast Atlantic
Online Access:http://dx.doi.org/10.1246/bcsj.20220070
https://academic.oup.com/bcsj/article-pdf/95/5/819/56317859/bcsj.20220070.pdf
Description
Summary:Abstract The convergent synthesis of the HIJKLMN-ring fragment of Caribbean ciguatoxin C-CTX-1, the major causative toxin for ciguatera fish poisoning in the Caribbean Sea and the Northeast Atlantic areas, is disclosed. The synthesis features a late-stage iron-catalyzed hydrogen atom transfer-initiated reductive olefin coupling to install the N-ring and a Suzuki–Miyaura coupling/thioacetalization strategy for the convergent assembly of the hexacyclic HIJKLM-ring skeleton.

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