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

被引:51
作者
Boukouvalas, John [1 ]
Wang, Jian-Xin [1 ]
Marion, Olivier [1 ]
Ndzi, Bruno [1 ]
机构
[1] Univ Laval, Dept Chim, Quebec City, PQ G1K 7P4, Canada
关键词
D O I
10.1021/jo0610154
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:6670 / 6673
页数:4
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