Zhu Lei, Mootoo David R
Department of Chemistry, Hunter College, 695 Park Avenue, New York, New York 10021, USA.
Org Lett. 2003 Sep 18;5(19):3475-8. doi: 10.1021/ol0352761.
[reaction: see text] A convergent approach to the synthesis of the bis-tetrahydrofuran (THF) components of the nonadjacently linked THF-containing acetogenins is illustrated in the synthesis of 2, a potential intermediate for the antitumor agent bullatanocin (squamostatin C). The plan centers on the olefin cross-metathesis of THF allylic alcohol derivatives 3 and 4 as the key segment coupling step and the assembly of 3 and 4 through the iodoetherification of 1,2-O-isopropylidene-5-alkene precursors.
[反应：见正文] 在2的合成中展示了一种用于合成非相邻连接的含四氢呋喃（THF）的产乙酸素的双四氢呋喃（THF）组分的汇聚方法，2是抗肿瘤剂布拉他诺辛（鲨他汀C）的潜在中间体。该方案以四氢呋喃烯丙醇衍生物3和4的烯烃交叉复分解作为关键的片段偶联步骤，并通过1,2-O-异亚丙基-5-烯烃前体的碘醚化反应来组装3和4。
