Pheromone Synthesis, CXL. Synthesis of Four Macrolide Pheromones to Define the Scope and Limitation of Enzymatic Macrolactonization

Abstract

Abstract The macrolides, ( R )‐ferrulactone II ( 2 ), ( Z )‐3‐dodecen‐12‐olide ( 3 ) and (5 Z ,13 R )‐5‐tetradecen‐13‐olide ( 4 ), could be synthesized by enzymatic macrolactonization with lipases by starting from (±)‐ 12 , 17 and (±)‐ 24 , respectively. Ferrulactone I ( 1 ) was prepared by the Corey macrolactonization, and the S enantiomers of 2 and 4 by chemical macrolactonization of ( S )‐ 11 and ( S )‐ 23 , respectively.