178. An Efficient Enantioselective Synthesis of (–)-Serricorole
     Oppolzer, W.; Rodriguez, I.
     Helv. Chim. Acta 1993, 76, 1275-1281

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 dihydropyranone14.

DOI : 10.1002/hlca.19930760314 

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