American Chemical Society
jo0610154_si_002.pdf (13.13 MB)

Synthesis and Stereochemistry of the Antitumor Diterpenoid (+)-Zerumin B

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journal contribution
posted on 2006-08-18, 00:00 authored by John Boukouvalas, Jian-Xin Wang, Olivier Marion, Bruno Ndzi
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 isolated from the plant Renealmia alpinia.