Stereoselective assembly of a 1,3-diene via coupling between an allenic acetate and a (B)-alkylborane: synthetic studies on amphidinolide B1.
Stereoselective assembly of a 1,3-diene via coupling between an allenic acetate and a (B)-alkylborane: synthetic studies on amphidinolide B1.
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通过联二烯乙酸酯和 (B)-烷基硼烷之间的偶联立体选择性组装 1,3-二烯：amphidinolide B1 的合成研究。
DOI：
10.1021/ol051175m
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发表时间：
2005
期刊：
影响因子：
5.2
通讯作者：
Crews,CraigM
中科院分区：
文献类型：
--
作者：
Mandal,AmitK;SchneeklothJr,JohnS;Crews,CraigM
本文报道了用于全合成两性霉素B_1的三个片段的制备。C16立体化学由不对称烯丙基烷基化确定。C21和C25立体异构中心通过对映选择性/非对映选择性双烯丙基化反应设置。C9构型通过不对称杂烯反应设定。通过碘离子介导的SN 2 '反应合成了一种不同取代的立体定向的1，3-二烯碘化物。还报道了一种通过偶联联丙二烯乙酸酯和（B）-烷基硼烷来立体选择性组装1，3-二烯的新方法。
The preparation of three fragments for the total synthesis of amphidinolide B1 has been described. The C16 stereochemistry was set by asymmetric allylic alkylation. C21 and C25 stereogenic centers were set by an enantioselective/diastereoselective double allylation reaction. The C9 configuration was set by an asymmetric heteroene reaction. A differentially substituted stereodefined 1,3-diene iodide was synthesized by iodide-mediated SN2‘ reaction. A novel stereoselective method to assemble a 1,3-diene by coupling an allenic acetate and (B)-alkylborane is also reported.