Tetrahedron letters

On the construction of 2-substituted 1, 4-diacetoxybutadiene moiety: application to the synthesis of (±)-caulerpenyne

L Commeiras, M Santelli, JL Parrain

Index: Commeiras, Laurent; Santelli, Maurice; Parrain, Jean-Luc Tetrahedron Letters, 2003 , vol. 44, # 11 p. 2311 - 2314

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Citation Number: 21

Abstract

The synthesis of 2-substituted 1, 4-diacetoxybutadiene derivatives with a partial control of stereochemistry is described from two potentially precursor enals by a judicious choice of experimental conditions (Ac2O/DMAP in Et3N). These conditions have been successfully applied in the first total synthesis of caulerpenyne.

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