Total synthesis of the Fusarium toxin equisetin: proof of the stereochemical relationship of the tetramate and terpenoid sectors

A total synthesis of the Fusarium mycotoxin equisetin, in a manner that establishes its stereochemistry, is described. The key steps involve a lactonic variation of the ester enolate Claisen rearrangement and a novel construction of a 1-acyltetramic acid from an L-N-methylserine derivative and a bet...

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Bibliographic Details
Published in:Journal of the American Chemical Society 1989-10, Vol.111 (21), p.8231-8236
Main Authors: Turos, Edward, Audia, James E, Danishefsky, Samuel J
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Summary:A total synthesis of the Fusarium mycotoxin equisetin, in a manner that establishes its stereochemistry, is described. The key steps involve a lactonic variation of the ester enolate Claisen rearrangement and a novel construction of a 1-acyltetramic acid from an L-N-methylserine derivative and a beta -keto ester.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja00203a026