Asymmetric Synthesis of β, γ-Disubstituted γ-Lactones

Acta Chimica Sinica ›› 2004, Vol. 62 ›› Issue (18): 1794-1800. Previous Articles Next Articles

β,γ-二取代γ-内酯的不对称合成

黄培强, 于贤勇, 刘秀平

厦门大学化学系, 化学生物学福建省重点实验室, 厦门, 361005

投稿日期:2004-04-01 修回日期:2004-08-15 发布日期:2014-02-17
通讯作者: 黄培强,E-mail:pqhuang@xmu.edu.cn E-mail:pqhuang@xmu.edu.cn
基金资助:
国家自然科学基金(Nos.20272048;203900505)和教育部科学技术研究重点项目资助课题.

Asymmetric Synthesis of β, γ-Disubstituted γ-Lactones

HUANG Pei-Qiang, YU Xian-Yong, LIU Xiu-Ping

Department of Chemistry, Fujian Province Key Laboratory of Chemical Biology, Xiamen University, Xiamen 361005

Received:2004-04-01 Revised:2004-08-15 Published:2014-02-17

Abstract

A flexible approach to γ-alkyl β-htdroxy γ-lactone is described. Tow of the lactones were converted into blastmycinone and trans-whisky lactone respectively. The method features a NaBH4 mediated reductive ring-opening of N,O-acetals, which is obtained via a regioselective Grignard reagent addition with (S)-N,O-dibenzylmalimide followed by lactoneization. The flexibility of the method allows the introduction of various γ-alkyl side chains by Grignard reagents addition.

Key words: (S)-malic acid, blastmycinone, trans-whisky lactone, reduction, Grignard reagent, N,O-acetal

Cite this article

HUANG Pei-Qiang, YU Xian-Yong, LIU Xiu-Ping. Asymmetric Synthesis of β, γ-Disubstituted γ-Lactones[J]. Acta Chimica Sinica, 2004, 62(18): 1794-1800.

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β,γ-二取代γ-内酯的不对称合成

Asymmetric Synthesis of β, γ-Disubstituted γ-Lactones

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