Synthesis and stereochemistry of the antitumor diterpenoid (+)-zerumin B

J Boukouvalas, JX Wang, O Marion…

Index: Boukouvalas, John; Wang, Jian-Xin; Marion, Olivier; Ndzi, Bruno Journal of Organic Chemistry, 2006 , vol. 71, # 17 p. 6670 - 6673

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Citation Number: 53

Abstract

Starting from commercially available (+)-sclareolide, the first synthesis of zerumin B was achieved by a concise, highly efficient pathway featuring stereoselective addition of a new silyloxyfuryltitanium reagent to an aldehyde intermediate and silyloxyfuran oxyfunctionalization as key steps. The synthesis established the relative and absolute configuration of zerumin B along with its identity with a purportedly new diterpenoid ...