Internal Diels−Alder Cycloaddition with a Z-Dienophile: Synthesis of (±)-α-Oplopenone
The Journal of Organic Chemistry1998Vol. 63(22), pp. 7953–7956
Citations Over Time
Abstract
The preparation of the Z-triene 3 is described. Internal Diels−Alder cycloaddition of 3 proceeds smoothly in the presence of BF3·OEt2 to give 2. Ketone 2 is converted by epimerization, carbonyl extrusion, and homologation to the sesquiterpene (±)-α-oplopenone (1).