4.4 Article

A convergent total synthesis of epolactaene: an application of the bridgehead oxiranyl anion strategy

Journal

TETRAHEDRON
Volume 59, Issue 49, Pages 9743-9758

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2003.09.021

Keywords

epolactaene; epoxylactone; TBAF; aldol reaction

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The generation and reaction of a lactone-derived oxiranyl anion is described. The aldol-type reaction of the epoxylactone and aldehydes was accomplished by a two-step procedure via the trimethylsilyl epoxylactone. The application of this methodology to the total synthesis of (+)-epolactaene and its analogs is described. (C) 2003 Elsevier Ltd. All rights reserved.

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