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Total Synthesis of seco-Plakortolide E and (−)-ent-Plakortolide I: Absolute Configurational Revision of Natural Plakortolide I

Author:
Barnych, Bogdan, Vatèle, Jean-Michel
Source:
Organic letters 2012 v.14 no.2 pp. 564-567
ISSN:
1523-7052
Subject:
chemical reactions, chemical structure, diastereoselectivity, organic compounds, regioselectivity
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.
Agid:
5784494