An Approach to <i>seco</i>-Prezizaane Sesquiterpenoids: Enantioselective Total Synthesis of (+)‑1<i>S</i>‑Minwanenone

Abstract

A strategy of general applicability toward <i>seco</i>-prezizaane sesquiterpenes, from a chiral, tricyclic synthon, readily available via an enzymatic resolution step from the Diels–Alder adduct of cyclopentadiene and <i>p</i>-benzoquinone, has been devised. Our approach enables harnessing of the stereochemical proclivities of the norbornyl system to install the desired stereochemistry at the key stereogenic centers. Recourse to an interesting stratagem to realign a stereochemical divergence into stereoreconvergence forms the cornerstone of our successful approach. The first total synthesis of (+)-1<i>S</i>-minwanenone, a prototypical member of <i>seco</i>-prezizaane subclass, has been accomplished