Issue 7, 2018

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

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

Supplementary files

Article information

Article type
Paper
Submitted
15 Nov 2017
Accepted
15 Jan 2018
First published
15 Jan 2018

Org. Biomol. Chem., 2018,16, 1118-1125

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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