Lewis Acid catalyzed Diels-Alder Reactions of S-(+)-Carvone with Silyloxy Dienes. Total Synthesis of (+)-α-Cyperone.

Article abstract of DOI:10.1016/S0040-4020(01)92253-7

The Diels-Alder reactions of S-(+)-carvone with 2-trimethylsilyloxy-1,3-butadiene, 3-trimethylsilyloxy-1,3-pentadiene and 2-tert-butyldimethylsilyloxy-3-methyl-1,3-butadiene with ethylaluminium dichloride as catalyst are described.The synthetic value of the adducts is demonstrated by the total synthesis of (+)-α-cyperone from one of the adducts. Key Words: S-(+)-carvone, silyloxy dienes, Lewis acid catalysis, Diels-Alder reaction, (+)-α-cyperone