Journal of the American Chemical Society

Asymmetric Total Synthesis of (−)-Amphidinolide V through Effective Combinations of Catalytic Transformations

I Volchkov, D Lee

Index: Volchkov, Ivan; Lee, Daesung Journal of the American Chemical Society, 2013 , vol. 135, # 14 p. 5324 - 5327

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Citation Number: 23

Abstract

An asymmetric total synthesis of (−)-amphidinolide V was accomplished. The synthesis features a base-catalyzed alkynyl silane alcoholysis/ring-closing enyne metathesis sequence for facile construction of a 1, 3-diene motif. A diene RCM followed by a ring- contractive allylic transposition of cyclic silyl ethers was incorporated for the stereoselective installation of a functionalized 1, 5-diene subunit. An efficient proline-mediated direct ...