Stereoselective synthesis of octahydrocyclohepta[c]pyran-6(1H)-one scaffolds through a Prins/alkynylation/hydration sequence

Abstract

Aldehydes undergo a smooth coupling with (E/Z)-non-3-en-8-yn-1-ol in the presence of 10 mol% of CuX and BF₃·OEt₂ under mild conditions to produce a novel class of octahydrocyclohepta[c]pyran-6(1H)-one derivatives in good yields with excellent diastereoselectivity through a sequential Prins/alkynylation/hydration. This is the first report on the termination of Prins cyclization with a tethered alkyne.