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Synthetic Studies on Ciguatoxin: A Convergent Strategy for Construction of the F–M Ring Framework
Author(s) -
Inoue Masayuki,
Sasaki Makoto,
Tachibana Kazuo
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980420)37:7<965::aid-anie965>3.0.co;2-p
Subject(s) - ciguatoxin , intramolecular force , ring (chemistry) , chemistry , convergent synthesis , acetal , stereochemistry , reformatsky reaction , natural product , organic chemistry , fish <actinopterygii> , biology , fishery
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.