An Efficient Enantioselective Synthesis of (—)‐Serricorole

Abstract

Abstract The cigarette beetle pheromone (–)‐serricorole ( 1 ) has been synthesized in 23% overall yield by an eight‐step sequence starting from N ‐propionylsultam 3 . The synthesis features asymmetric anti ‐ and syn ‐aldolizations 3 → 4 and 8 → 9 , a non‐destructive N ‐acylsultam cleavage with lithiated ethylphenylsulfone ( 10 → 12 ), and the smooth, Ti‐mediated cyclization of β‐acyloxy‐ketone 2 to dihydropyranone 14 .