Study demonstrates construction of a 1-oxaspiro skeleton from cyclopropane and cycloheptanone, highlighting unique structural attributes.
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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Suzuki et al. (2025) studied this question.
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