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. 2013 Dec 6;3(6):288–294. doi: 10.1007/s13659-013-0080-1

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

Yang Yang 1,2,✉
PMCID: PMC4131603

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. graphic file with name 13659_2013_80_Article_Fig1_HTML.jpg

Electronic Supplementary Material

Supplementary material is available for this article at 10.1007/s13659-013-0080-1 and is accessible for authorized users.

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

Electronic supplementary material

13659_2013_80_MOESM1_ESM.pdf (2.7MB, pdf)

Supplementary material, approximately 2.73 MB.

Footnotes

This article is published with open access at Springerlink.com

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Supplementary Materials

13659_2013_80_MOESM1_ESM.pdf (2.7MB, pdf)

Supplementary material, approximately 2.73 MB.

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