Enantioselective synthesis of Anomala osakanapheromone and Janus integerpheromone: a flexible approach to chiral γ-butyrolactones†
Li Lin,Qiangyang Zhao,A-Ni Li,Fengbo Ren,Fanzhi Yang
Organic & Biomolecular Chemistry Pub Date : 07/31/2009 00:00:00 , DOI:10.1039/B909418K
Abstract

The enantioselective synthesis of Anomala osakanapheromone and Janus integerpheromone has been achieved without using any protecting groups. The synthesis involved using an asymmetric alkynylation to obtain γ-hydroxy-α,β-acetylenic esters with high ee (84%) and yields (∼80%), followed by selective hydrogenation and lactonization in high overall yields (87% and 89%).

Graphical abstract: Enantioselective synthesis of Anomala osakanapheromone and Janus integerpheromone: a flexible approach to chiral γ-butyrolactones