Asymmetric total synthesis of (-)-rossinone A

The asymmetric total synthesis of (-)-rossinone A, a meroterpene exhibiting a range of pharmacologically important biological activities, has been accomplished for the first time from geraniol by a concise eight step sequence that involves the Horner-Wadsworth-Emmons reaction of an aldehyde derived from a geranylated hydroquinone intermediate with a chiral phosphonate prepared via the highly diastereoselective Davis oxidation of a known oxazolidinone derivative. (c) 2021 Elsevier Ltd. All rights reserved.

Automated summary

The asymmetric total synthesis of (-)-rossinone A, a meroterpene with pharmacologically important biological activities, has been achieved for the first time from geraniol in a concise eight step sequence involving the Horner-Wadsworth-Emmons reaction of an aldehyde derived from a geranylated hydroquinone intermediate with a chiral phosphonate prepared via the highly diastereoselective Davis oxidation of a known oxazolidinone derivative.