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Citation: WU Ming-Hu, CHEN Zu-Xing, LI Yan, YANG Gui-Chun. Diastereoselective Synthesis of (±)-trans-Cognac Lactone[J]. Chinese Journal of Applied Chemistry, ;2000, 17(1): 113-114. shu

Diastereoselective Synthesis of (±)-trans-Cognac Lactone

1.
1. Department of Chemistry, Xianning Normal College, Xianning 437005;
2.
2. Faculty of Chemistry and Material Science, Hubei University, Wuhan

Received Date: 14 July 1999
Available Online: 8 October 1999
Fund Project: 湖北省教委重点资助课题(96A077) (96A077)

A new route to diastereoselective synthesis of (±)-trans-cognac lactone in five steps is described. The key intermediate methyl 3-formylbutanoate (4) was prepared from methy lcro tonate (1) in high yield.Addition of n-amylmagnesium bromide/cuprous iodide to the fo rmyl of (4), through fo rmation of seven-membered ring chelate which involved both carbonyl function groups of (4) and MgX or Cu as a central metal, afforded (±)-trans-cognac lactone (5) in 52% yield with high diastereoselectivity: ratio of trans to cisisomers was 97:3 by GC. The procedure had advantages of simplicity, high stereoselectivity of products and mild reaction conditions.
- trans-cognac lactone,
- butyrolactone,
- diastereoselective synthesis
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