Tetrahedron Letters

A concise enantioselective synthesis of (+)-goniodiol and (+)-8-methoxygoniodiol via Co-catalyzed HKR of anti-(2SR, 3RS)-3-methoxy-3-phenyl-1, 2-epoxypropane

INC Kiran, RS Reddy, G Suryavanshi, A Sudalai

Index: Kiran, I.N. Chaithanya; Reddy, R. Santhosh; Suryavanshi, Gurunath; Sudalai, Arumugam Tetrahedron Letters, 2011 ,  vol. 52,  # 3  p. 438 - 440

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Citation Number: 23

Abstract

A short, enantioselective synthesis of (+)-goniodiol and (+)-8-methoxygoniodiol, cytotoxic styryllactones, has been achieved in high optical purities (99% ee). The strategy employs Co- catalyzed HKR of racemic anti-(2SR, 3RS)-3-methoxy-3-phenyl-1, 2-epoxypropane and Lewis acid-mediated diastereoselective allylation of aldehyde as chiral inducing key reactions.