Issue 19, 2016
From the journal:

Organic & Biomolecular Chemistry

Epimerization of C5 of an N-hydroxypyrrolidine in the synthesis of swainsonine related iminosugars†

Bao-Chen Qian,ae   Akiko Kamori,b   Kyoko Kinami,b   Atsushi Kato,*b   Yi-Xian Li,a   George W. J. Fleetcd  and  Chu-Yi Yu*ad  

* Corresponding authors

a Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
E-mail: yucy@iccas.ac.cn

b Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
E-mail: kato@med.u-toyama.ac.jp

c Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, UK

d National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, PR China

e University of Chinese Academy of Sciences, Beijing 100049, China

Abstract

Epimerization of C5 of an N-hydroxypyrrolidine ring by regioselective oxidation to a nitrone followed by diastereoselective reduction provides a new approach to the synthesis of swainsonine and related compounds. The only protection in the synthesis of the potent mannosidase inhibitor DIM (1,4-dideoxy-1,4-imino-D-mannitol) was the acetonation of D-mannose.

Graphical abstract: Epimerization of C5 of an N-hydroxypyrrolidine in the synthesis of swainsonine related iminosugars

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Article information

DOI
https://doi.org/10.1039/C6OB00531D
Article type
Paper
Submitted
10 Mar 2016
Accepted
14 Apr 2016
First published
14 Apr 2016

Org. Biomol. Chem., 2016,14, 4488-4498

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Epimerization of C5 of an N-hydroxypyrrolidine in the synthesis of swainsonine related iminosugars

B. Qian, A. Kamori, K. Kinami, A. Kato, Y. Li, G. W. J. Fleet and C. Yu, Org. Biomol. Chem., 2016, 14, 4488 DOI: 10.1039/C6OB00531D

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