Premium Synthetic Studies on Ciguatoxin: A Convergent Strategy for Construction of the F–M Ring Framework
Inoue Masayuki,
Sasaki Makoto,
Tachibana Kazuo
Publication year1998
Publication title
angewandte chemie international edition
Resource typeJournals
Abstract Exceptional neurotoxicity is associated with ciguatoxin. The ciguatoxin mimic 1 , which contains the F–M framework of the natural product, has been prepared through a convergent synthesis. The two key steps were a Lewis acid mediated intramolecular reaction of a γ ‐alkoxyallylsilane with an acetal group and an SmI 2 ‐mediated intramolecular Reformatsky reaction that permitted construction of the annelated hexahydrooxonin ring system.
Subject(s)acetal , biology , chemistry , ciguatoxin , convergent synthesis , fish <actinopterygii> , fishery , intramolecular force , natural product , organic chemistry , reformatsky reaction , ring (chemistry) , stereochemistry , total synthesis
SCImago Journal Rank5.831

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