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

doi:10.1007/s13659-013-0080-1

Natural Products and Bioprospecting ›› 2013, Vol. 3 ›› Issue (6): 288-294.DOI: 10.1007/s13659-013-0080-1

• Regular Article • Previous Articles

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:2018-02-11 Published:2013-12-24

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

通讯作者: Yang YANG,E-mail:yangyangc@mail.kib.ac.cn

Abstract

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

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

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.

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.

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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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