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Total synthesis of seco-plakortolide E and (-)-ent-plakortolide I: absolute configurational revision of natural plakortolide I.

Authors
  • Barnych, Bogdan
  • Vatèle, Jean-Michel
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Jan 20, 2012
Volume
14
Issue
2
Pages
564–567
Identifiers
DOI: 10.1021/ol203185f
PMID: 22191515
Source
Medline
License
Unknown

Abstract

A first total synthesis of (-)-ent-plakortolide I and seco-plakortolide E was accomplished from (S)-2-methylglycidol. The relevant key reactions involve a diastereoselective Mukaiyama aldol reaction, a regioselective hydroperoxysilylation, and elaboration of the 1,2-dioxane ring by intramolecular Michael addition of a hydroperoxide group to a butenolide. This synthesis allowed the revision of the absolute configuration of plakortolide I and structural revision of plakortolide E.

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