Synthetic Studies of Spiroschincarins: Construction of 1-Oxaspiro[6.6]tridecanone Skeleton with All-cis Cyclopropane Moiety

螺环辛卡林类化合物的合成研究:构建具有全顺式环丙烷部分的1-氧杂螺[6.6]十三烷酮骨架

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Abstract

Spiroschincarins are triterpenoids characterized by a hexacyclic structure with a unique 1-oxaspiro[6.6]tridecanone skeleton and an all-cis substituted cyclopropane moiety. In the present study, this core skeleton was convergently synthesized by coupling all-cis-substituted cyclopropane and cycloheptanone fragments. The keys for its construction were the use of a conformationally limited substrate for lactonization and control of chelation for reducing the double bond on the spiro-lactone ring.

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