天然氨基酸四氢β-氨基丙腈的全合成及绝对构型

Total synthesis and absolute configuration of the natural amino acid tetrahydrolathyrine.

作者信息

Benohoud Meryem, Leman Loic, Cardoso Silvia H, Retailleau Pascal, Dauban Philippe, Thierry Josiane, Dodd Robert H

机构信息

Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, UPR 2301, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.

出版信息

J Org Chem. 2009 Aug 7;74(15):5331-6. doi: 10.1021/jo900800x.

DOI:10.1021/jo900800x

PMID:19572523

Abstract

The natural product tetrahydrolathyrine has been synthesized through an iminoiodane-mediated aziridination of a (2S)-allylglycinol derivative, which provided a 2:3 mixture of diastereoisomers. One of these diastereoisomers was converted to the natural product and the other to its C-4 epimer. The C-4 configuration was established from NOESY NMR analysis and X-ray structure of compounds derived from the non-natural diastereoisomer. Thus, tetrahydrolathyrine was shown to have the (2S,4R) absolute configuration.

摘要

天然产物四氢β-氨基丙腈已通过亚胺碘烷介导的(2S)-烯丙基甘醇衍生物的氮杂环丙烷化反应合成，该反应得到了非对映异构体的2:3混合物。其中一种非对映异构体被转化为天然产物，另一种则转化为其C-4差向异构体。通过NOESY核磁共振分析和源自非天然非对映异构体的化合物的X射线结构确定了C-4构型。因此，四氢β-氨基丙腈显示具有(2S,4R)绝对构型。