Two Concise Enantioselective Total Syntheses of (-)-Glabrescol Implicate Alternative Biosynthetic Pathways Starting from Squalene

[摘要]：The C-2-symmetric (-)-glabrescol was synthesized in two steps from (10S,11R)-dihydroxy-10,11-dihydrosqualene or squalene with 50% or 10% overall yields, respectively. These highly efficient and biomimetic syntheses employed a base-promoted middle-to-terminal double epoxide-opening cascade, which constructs the five tetrahydrofuran rings in glabrescol in one operation.

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