Tetrahedron letters

First stereoselective total synthesis of (6R)-6-[(4R, 6R)-4, 6-dihydroxy-10-phenyldec-1-enyl]-5, 6-dihydro-2H-pyran-2-one

PR Krishna, R Srinivas

Index: Radha Krishna, Palakodety; Srinivas, Ravula Tetrahedron Letters, 2007 , vol. 48, # 11 p. 2013 - 2015

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Citation Number: 33

Abstract

A stereoselective total synthesis of (6R)-6-[(4R, 6R)-4, 6-dihydroxy-10-phenyldec-1-enyl]-5, 6-dihydro-2H-pyran-2-one is reported. The strategy utilizes an iterative Jacobsen hydrolytic kinetic resolution, ring opening with a chiral propargylic synthon and a preferential (Z)-Wittig olefination reaction and lactonization as the key steps.

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