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Issue 19, 2016
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Epimerization of C5 of an N-hydroxypyrrolidine in the synthesis of swainsonine related iminosugars

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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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Publication details

The article was received on 10 Mar 2016, accepted on 14 Apr 2016 and first published on 14 Apr 2016


Article type: Paper
DOI: 10.1039/C6OB00531D
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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