Stereoselective Assembly of a 1,3-Diene via Coupling between an Allenic Acetate and a (<i>B</i>)-Alkylborane: Synthetic Studies on Amphidinolide B1
作者:Amit K. Mandal、John S. Schneekloth,、Craig M. Crews
DOI:10.1021/ol051175m
日期:2005.8.1
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 S(N)2' reaction. A novel stereoselective method
已经描述了用于全部合成两性霉素B1的三个片段的制备。C16立体化学是通过不对称的烯丙基烷基化来设定的。通过对映选择性/非对映选择性双烯丙基化反应设定C21和C25立体异构中心。C9构型是通过不对称杂烯反应设定的。通过碘化物介导的S(N)2'反应合成了差异取代的立体定义的1,3-二烯碘化物。还报道了通过偶联乙酸烯丙酯和(B)-烷基硼烷来组装1,3-二烯的新颖的立体选择性方法。[结构:见文字]