Cyclopentenones from β, ε-Diketo Phosphonates. Synthesis of cis-Jasmone

Abstract

The synthesis of cyclopentenones has become an important area of research in recent years and various ingenious routes to these compounds have been developed. ¹ Our interest in the preparation of functionalized hydrindenones (eq. 3) for synthetic work related to vernolepin ² led us to investigate the cyclization of β, ε-diketo phosphonates as a general route to functionalized cyclo-pentenones. ³ We report here the use of this approach in the preparation of 3 as well as an efficient (∼60% overall yield) synthesis of the important perfumery agent cis-jasmone 12.