Synthesis of cis-hydrindan-2,4-diones bearing an all-carbon quaternary center by a Danheiser annulation

Beilstein J Org Chem. 2018 Oct 9:14:2597-2601. doi: 10.3762/bjoc.14.237. eCollection 2018.

Abstract

A straightforward synthetic entry to functionalized hydrindane compounds based on a rapid assembly of the core nucleus by a Danheiser cycloaddition is reported. Valuable bicyclic building blocks containing the fused five and six-membered carbocyclic ring system can be achieved in only four steps from a simple acyclic β-keto ester.

Keywords: Danheiser annulation; alkaloid; decahydroquinoline.