State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
Org Lett. 2012 Oct 5;14(19):5114-7. doi: 10.1021/ol302386g. Epub 2012 Sep 19.
A Lewis acid promoted tandem semipinacol-type 1,2-carbon migration/aldol reaction of trimethylsilane-protected vinylogous α-ketols with aldehyde or dimethyl acetals is reported. This reaction provides a direct and rapid way for the construction of 6-substituted spiro[4.5]decanes which extensively exist in Daphniphyllum alkaloids. By the use of this method, further construction of a [5-6-7] all-carbon tricyclic core of Calyciphylline A-type alkaloids was also completed.
一种路易斯酸促进的三甲基硅烷保护的乙烯基酮式α-酮醇与醛或二甲缩醛的串联半频哪醇型 1,2-碳迁移/羟醛反应被报道。该反应为构建广泛存在于防己科生物碱中的 6-取代螺[4.5]癸烷提供了一种直接而快速的方法。通过使用该方法，还完成了 Calyciphylline A 型生物碱中[5-6-7]全碳三环核心的进一步构建。
