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Creators/Authors contains: "Wang, Ye‐Cheng"

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  1. ; ; (, Angewandte Chemie International Edition)
    Abstract Massarinolin A and purpurolides are bioactive bergamotane sesquiterpenes condensed with a variety of synthetically challenging ring systems: a bicyclo[3.1.1]heptane, an oxaspiro[3.4]octane, and a dioxaspiro[4.4]nonane (oxaspirolactone). Herein, we report the first enantioselective total syntheses of massarinolin A, purpurolides B, D, E, and 2,3‐deoxypurpurolide C. Our synthesis and computational analysis also led to a structural revision of massarinolin A. The divergent approach features an enantioselective organocatalyzed Diels–Alder reaction to install the first stereogenic center in highee, a scalable flow photochemical Wolff rearrangement to build the key bicyclo[3.1.1]heptane, a furan oxidative cyclization to form the oxaspirolactone, a late‐stage allylic C−H oxidation, and a Myers’ NBSH‐promoted sigmatropic elimination to install theexomethylene group of massarinolin A. 
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