Total synthesis and determination of the absolute configuration of a natural analgesic: crotonine

doi:10.1007/s13659-013-0080-1

应用天然产物 ›› 2013, Vol. 3 ›› Issue (6): 288-294.DOI: 10.1007/s13659-013-0080-1

• Regular Article • 上一篇

Total synthesis and determination of the absolute configuration of a natural analgesic: crotonine

Yang YANG^a,b

a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b Graduate University of Chinese Academy of Sciences, Beijing 100049, China

收稿日期:2013-10-09 修回日期:2013-11-21 出版日期:2013-12-24 发布日期:2018-02-11
通讯作者: Yang YANG,E-mail:yangyangc@mail.kib.ac.cn

Total synthesis and determination of the absolute configuration of a natural analgesic: crotonine

Yang YANG^a,b

a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b Graduate University of Chinese Academy of Sciences, Beijing 100049, China

Received:2013-10-09 Revised:2013-11-21 Online:2013-12-24 Published:2018-02-11

摘要/Abstract

摘要： We report the first total synthesis of four possible absolute configurations and four other regional isomers of a naturally occurring alkaloid crotonine, which was isolated from Croton tiglium L. (Euphoriaceae) without elucidation of its absolute configuration. The concise five-step route with a chirally poor and regioselective strategy starting from monosaccharides was established, and the absolute structure of the natural crotonine was determined by comparison of the NMR spectra and optical rotations of the synthetic products.

关键词: total synthesis, crotonine, 2-(furan-2-yl)-5-(2,3,4-trihydroxy-butyl)-1,4-diazine, Croton tiglium L. (Euphoriaceae), analgesics

Abstract: We report the first total synthesis of four possible absolute configurations and four other regional isomers of a naturally occurring alkaloid crotonine, which was isolated from Croton tiglium L. (Euphoriaceae) without elucidation of its absolute configuration. The concise five-step route with a chirally poor and regioselective strategy starting from monosaccharides was established, and the absolute structure of the natural crotonine was determined by comparison of the NMR spectra and optical rotations of the synthetic products.

Key words: total synthesis, crotonine, 2-(furan-2-yl)-5-(2,3,4-trihydroxy-butyl)-1,4-diazine, Croton tiglium L. (Euphoriaceae), analgesics

Yang YANG. Total synthesis and determination of the absolute configuration of a natural analgesic: crotonine[J]. 应用天然产物, 2013, 3(6): 288-294.

Yang YANG. Total synthesis and determination of the absolute configuration of a natural analgesic: crotonine[J]. Natural Products and Bioprospecting, 2013, 3(6): 288-294.

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Total synthesis and determination of the absolute configuration of a natural analgesic: crotonine

Total synthesis and determination of the absolute configuration of a natural analgesic: crotonine

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