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Total Synthesis of seco-Plakortolide E and (−)-ent-Plakortolide I: Absolute Configurational Revision of Natural Plakortolide I
- Barnych, Bogdan, Vatèle, Jean-Michel
- Organic letters 2012 v.14 no.2 pp. 564-567
- chemical reactions, chemical structure, diastereoselectivity, organic compounds, regioselectivity
- 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.