An Approach to seco-Prezizaane Sesquiterpenoids: Enantioselective Total Synthesis of (+)?1S?Minwanenone

摘要

A strategy of general applicability toward seco-prezizaanensesquiterpenes, from a chiral, tricyclic synthon, readily available via annenzymatic resolution step from the Diels−Alder adduct of cyclopentadienenand p-benzoquinone, has been devised. Our approach enables harnessing ofnthe stereochemical proclivities of the norbornyl system to install the desirednstereochemistry at the key stereogenic centers. Recourse to an interestingnstratagem to realign a stereochemical divergence into stereoreconvergencenforms the cornerstone of our successful approach. The first total synthesis ofn(+)-1S-minwanenone, a prototypical member of seco-prezizaane subclass, hasnbeen accomplished.