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The Furan Shuffling Hypothesis: a Biogenetic Proposal for Eremophilane Sesquiterpenoids.

Angewandte Chemie 2019 March 23
Based on the structural similarities of the recently isolated eremophilane-type sesquiterpenoids microsphaeropsisin B and C and the iso-eremophilane periconianone C, we suggest a revised biogenetic hypothesis for C8-C11 connected iso-eremophilanes. In this communication, we provide strong experimental evidence corroborating our biogenetic proposal. The first enantioselective total syntheses of microsphaeropsisin B and C have been achieved starting from a known intermediate, whose synthesis has been elaborated in the course of the total synthesis of periconianone A in our group, and in a total of 15 steps starting from γ-hydroxy carvone. Mild reaction conditions for the subsequent α-ketol rearrangement not only allowed for our proposed conversion of microsphaeropsisin B to periconianone C, but also for the transition of microsphaeropsisin C to 4-epi-periconianone C.

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