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Issue 7, 2018
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Total synthesis of pipecolic acid and 1-C-alkyl 1,5-iminopentitol derivatives by way of stereoselective aldol reactions from (S)-isoserinal

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Abstract

A short synthesis of iminosugars and pipecolic acid derivatives has been realized through aldol addition of a pyruvate, a range of ketones and (S)-isoserinal, followed by catalytic reductive intramolecular amination. The stereoselective aldol reaction was achieved successfully by using tertiary amines or di-zinc aldol catalysts, thus constituting two parallel routes to optically pure products with good yields and high diastereoselectivities. These carbohydrate analogues may be the inhibitors of potent glycosidases and glycosyltransferases.

Graphical abstract: Total synthesis of pipecolic acid and 1-C-alkyl 1,5-iminopentitol derivatives by way of stereoselective aldol reactions from (S)-isoserinal

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Publication details

The article was received on 15 Nov 2017, accepted on 15 Jan 2018 and first published on 15 Jan 2018


Article type: Paper
DOI: 10.1039/C7OB02797D
Citation: Org. Biomol. Chem., 2018,16, 1118-1125
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    Total synthesis of pipecolic acid and 1-C-alkyl 1,5-iminopentitol derivatives by way of stereoselective aldol reactions from (S)-isoserinal

    S. Baś, R. Kusy, M. Pasternak-Suder, C. Nicolas, J. Mlynarski and O. R. Martin, Org. Biomol. Chem., 2018, 16, 1118
    DOI: 10.1039/C7OB02797D

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