Issue 93, 2022

De novo asymmetric Achmatowicz approach to oligosaccharide natural products

Abstract

The development and application of the asymmetric synthesis of oligosaccharides from achiral starting materials is reviewed. This de novo asymmetric approach centers around the use of asymmetric catalysis for the synthesis of optically pure furan alcohols in conjunction with Achmatowicz oxidative rearrangement for the synthesis of various pyranones. In addition, the use of a diastereoselective palladium-catalyzed glycosylation and subsequent diastereoselective post-glycosylation transformation was used for the synthesis of oligosaccharides. The application of this approach to oligosaccharide synthesis is discussed.

Graphical abstract: De novo asymmetric Achmatowicz approach to oligosaccharide natural products

Article information

Article type
Feature Article
Submitted
26 sep 2022
Accepted
28 okt 2022
First published
28 okt 2022

Chem. Commun., 2022,58, 12913-12926

Author version available

De novo asymmetric Achmatowicz approach to oligosaccharide natural products

S. Kim, J. Oiler, Y. Xing and G. A. O’Doherty, Chem. Commun., 2022, 58, 12913 DOI: 10.1039/D2CC05280F

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