Enantioselective synthesis of Anomala osakana pheromone and Janus integer pheromone: a flexible approach to chiral γ-butyrolactones

Li Lin; Qiangyang Zhao; A-Ni Li; Fengbo Ren; Fanzhi Yang; Rui Wang

doi:10.1039/B909418K

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Organic & Biomolecular Chemistry

Issue 18, 2009

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Enantioselective synthesis of Anomala osakana pheromone and Janus integer pheromone: a flexible approach to chiral γ-butyrolactones

Li Lin , Qiangyang Zhao , A-Ni Li , Fengbo Ren , Fanzhi Yang and Rui Wang

Org. Biomol. Chem., 2009, 7, 3663-3665

DOI: 10.1039/B909418K
Received 21 May 2009, Accepted 21 Jul 2009
First published on the web 31 Jul 2009

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The enantioselective synthesis of Anomala osakana pheromone and Janus integer pheromone 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 ( [similar] 80%), followed by selective hydrogenation and lactonization in high overall yields (87% and 89%).

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Li Lin
Qiangyang Zhao
A-Ni Li
Fengbo Ren
Fanzhi Yang
Rui Wang

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Organic & Biomolecular Chemistry

Enantioselective synthesis of Anomala osakana pheromone and Janus integer pheromone: a flexible approach to chiral γ-butyrolactones

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