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Tandem Semipinacol-Type 1,2-Carbon Migration/Aldol Reaction toward the Construction of [5–6–7] All-Carbon Tricyclic Core of Calyciphylline A‑Type Alkaloids

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posted on 2012-10-05, 00:00 authored by Ming Yang, Lin Wang, Zheng-He He, Shao-Hua Wang, Shu-Yu Zhang, Yong-Qiang Tu, Fu-Min Zhang
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.