4.4 Article

First total synthesis of salinipyrone A using highly stereoselective vinylogous Mukaiyama aldol reaction

Journal

TETRAHEDRON
Volume 68, Issue 45, Pages 9289-9292

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.08.035

Keywords

Aldol reaction; Wittig olifination; Cyclization; Salinipyrones; Pacificanones

Funding

  1. CSIR-UGC, New Delhi, India

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A synthetic approach for the total synthesis of salinipyrone A has been developed. Key steps involve the TiCl4-mediated vinylogous Mukaiyama aldol reaction (VMAR) of chiral ketene silyl N,O-acetal with propionaldyhyde, an aldol condensation, Witting olefination, and a cyclization. The synthesis proceeds in eight steps. (C) 2012 Elsevier Ltd. All rights reserved.

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