Synthesis of the C-1-C-17 Fragment of Amphidinolides C C2, C3, and F
Synthesis of the C-1-C-17 Fragment of Amphidinolides C C2, C3, and F
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DOI：
10.1021/ol4004838
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发表时间：
2013-04-05
期刊：
影响因子：
5.2
通讯作者：
Osnowski, Andrew P.
中科院分区：
文献类型：
--
作者：
Clark, J. Stephen;Yang, Guang;Osnowski, Andrew P.
已从反式-2，5-二取代二氢呋喃酮通过由金属卡宾产生的游离或金属结合的氧鎓叶立德的非对映选择性重排制备的，两环内酯C、C2、C3和F的C-1-C-17片段被构建。将二氢呋喃酮转化为对应于C-1-C-8骨架的醛，并通过乙烯基阴离子的亲核加成将其偶联到C-9-C-17单元。
The C-1-C-17 fragment of amphidinolides C, C2, C3, and F has been constructed from a trans-2,5-disubstituted dihydrofuranone prepared by diastereoselective rearrangement of a free or metal-bound oxonium ylide generated from a metal carbenoid. The dihydrofuranone was converted into an aldehyde corresponding to the C-1-C-8 framework, and this was coupled to the C-9-C-17 unit by nucleophilic addition of a vinylic anion.