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从 D-甘油醛出发全合成（-）-去氧紫堇林碱、（+）-2-表去氧紫堇林碱以及（2R,3R）-和（2R,3S）-3-羟基哌啶酸

Synthesis of (-)-deoxoprosophylline, (+)-2-epi-deoxoprosopinine, and (2R,3R)- and (2R,3S)-3-hydroxypipecolic acids from D-glycals.

机构信息

Department of Chemistry, Indian Institute of Technology Kanpur 208 016, India.

出版信息

J Org Chem. 2010 Jul 2;75(13):4608-11. doi: 10.1021/jo100489k.

DOI:10.1021/jo100489k
PMID:20524655
Abstract

New syntheses of (-)-deoxoprosophylline, (+)-2-epi-deoxoprosopinine, and (2R,3R)- and (2R,3S)-3-hydroxypipecolic acids are reported. Utilization of the chiral functionalities of Perlin aldehydes, derived from 3,4,6-tri-O-benzyl glycals, has been done along with chemoselective saturation of olefins and reductive aminations as key steps.

摘要

报告了 (-)-去氧紫堇林碱、(+)-2-表去氧紫堇林碱以及 (2R,3R)-和 (2R,3S)-3-羟基哌啶酸的新合成方法。利用了源自 3,4,6-三-O-苄基-葡萄糖醛酸的 Perlin 醛的手性官能团，并将烯烃的选择性饱和和还原胺化作为关键步骤。

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