Synthesis and stereochemistry of the antitumor diterpenoid (+)-zerumin B
Synthesis and stereochemistry of the antitumor diterpenoid (+)-zerumin B
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DOI：
10.1021/jo0610154
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发表时间：
2006-08-18
影响因子：
3.6
通讯作者：
Ndzi, Bruno
中科院分区：
文献类型：
--
作者：
Boukouvalas, John;Wang, Jian-Xin;Ndzi, Bruno
以市售的 (+)-香紫苏内酯为原料，通过简洁、高效的途径首次合成了 zerumin B，该途径以将新型甲硅烷氧基呋喃基钛试剂立体选择性加成到醛中间体中，并以甲硅烷氧基呋喃氧基官能化为关键步骤。该合成确定了zerumin B 的相对和绝对构型及其与从高山肾草中分离出的据称新二萜类化合物的特性。
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.