Total synthesis of seco-plakortolide E and (-)-ent-plakortolide I: absolute configurational revision of natural plakortolide I |
| |
Authors: | Barnych Bogdan Vatèle Jean-Michel |
| |
Institution: | Université Lyon 1, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), UMS 5246 CNRS, équipe SURCOOF, bat Raulin, 43 bd du 11 Novembre 1918, Villeurbanne Cedex, France. |
| |
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. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|