Direct and highly stereoselective synthesis of quinolizidine iminosugars promoted by L-proline-Et3N

Wen Yuan; Yang Pan; Xiaoke Zhang; Peng Liang; Jichao Zhang; Wei Jiao; Huawu Shao

doi:10.1039/C8OB01953C

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Direct and highly stereoselective synthesis of quinolizidine iminosugars promoted by l-proline-Et₃N†

Wen Yuan,^abc Yang Pan,^ac Xiaoke Zhang,^ac Peng Liang,^ac Jichao Zhang,^ac Wei Jiao^a and Huawu Shao

*^a

Author affiliations

* Corresponding authors

^a Natural Products Research Centre, Chengdu Institute of Biology, Chinese Academy of Science, Chengdu, China
E-mail: shaohw@cib.ac.cn
Fax: +86-028-82890288

^b Sichuan College of Traditional Chinese Medicine, Mianyang, Sichuan, China

^c University of Chinese Academy of Science, China

Abstract

A mild and effective method for the synthesis of polyhydroxylated quinolizidine iminosugars is described. The Mannich-type reaction of iminosugar C-glycosides with aldehyde in the presence of L-proline-Et₃N provides polyhydroxylated quinolizidine iminosugars, and desired products as the potential glucosidase inhibitors were obtained in good to excellent yields with excellent stereoselectivity.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C8OB01953C
Article type: Paper
Submitted: 10 Aug 2018
Accepted: 20 Nov 2018
First published: 22 Nov 2018

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Org. Biomol. Chem., 2018,16, 9230-9236

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Direct and highly stereoselective synthesis of quinolizidine iminosugars promoted by L-proline-Et₃N

W. Yuan, Y. Pan, X. Zhang, P. Liang, J. Zhang, W. Jiao and H. Shao, Org. Biomol. Chem., 2018, 16, 9230 DOI: 10.1039/C8OB01953C

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Organic & Biomolecular Chemistry