An Efficient Total Synthesis of (–)-(R), (+)-(S)-Lavandulol Pheromones and Their Derivatives through Proline Catalyzed Asymmetric a-Aminooxylation and [3,3] Claisen Rearrangement

摘要

An efficient total synthesis of the enantiomerically pure lavandulol pheromones viz. (–)-(R) and (+)-(S)-lavandulol, (– )-(R)-lavandulyl acetate, (–)-(R)-lavandulyl propionate, (+)-(S)- lavandulyl 2-methylbutanoate and (+)-(S)-lavandulyl senecioate is accomplished from nonchiral and chiral materials. The strategy utilizes a sequence of proline catalyzed asymmetric aaminooxylation and [3,3] Claisen rearrangement for stereodivergent synthesis of chiral C-2 unit containing 4-pentenols.