Diastereo- and enantioselective synthesis of allylsilane. A useful C-ring fragment of taxol
作者:Hiroyuki Kusama、Takeshi Mori、Ikuo Mitani、Hajime Kashima、Isao Kuwajima
DOI:10.1016/s0040-4039(97)00843-5
日期:1997.6
Enantioselective synthesis of a taxol C-ring fragment containing an allylsilane moiety is described. Diastereoselective [4 + 2] cycloaddition of the pyrone with (R)-t-butylbenzyl vinyl ether followed by appropriate transformations gave a mixture of two regioisomeric cyclohexenyl sulfides, which was converted to the title compound with almost complete diastereo- and enantioselectivities by treating
描述了含有烯丙基硅烷部分的紫杉醇C-环片段的对映选择性合成。吡喃酮与(R)-叔丁基苄基乙烯基醚的非对映选择性[4 + 2]环加成反应,然后进行适当的转化,得到两种区域异构的环己烯基硫化物的混合物,将其转化为标题化合物,并通过用李和4,4'-二牛逼-butylbiphenyl随后用甲基氯硅烷淬火。