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

Abstract

AbstractAn 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 α‐aminooxylation and [3,3] Claisen rearrangement for stereodivergent synthesis of chiral C‐2 unit containing 4‐pentenols.