Jump to main content
Jump to site search

Issue 17, 2019
Previous Article Next Article

Versatility of glycals in synthetic organic chemistry: coupling reactions, diversity oriented synthesis and natural product synthesis

Author affiliations

Abstract

Glycals, 1,2-unsaturated sugar derivatives, are versatile starting materials for the synthesis of natural products and the generation of novel structural features in Diversity Oriented Synthesis (DOS). The versatility of glycals in synthesis emanates, among others, from the presence of the ring oxygen and the enol-ether type unsaturation, the different types of stable conformations they can adopt depending on the nature of the protecting groups present and the ease with which the protecting groups of the three hydroxy groups could be tailored to suite for a desired manipulation. This review summarizes the literature on the different transformations of the endo glycals into biologically relevant compounds such as chromans, thiochromans, chromenes, thiochromenes, peptidomimetics, bridged benzopyrans etc., as well as on the use of glycals as chiral building blocks for the synthesis of various natural products such as aspicilin, reblastatin, diospongins, decytospolides, osmundalactones, paclitaxel, isatisine, D-fagomine, and spliceostatin, reported post 2014.

Graphical abstract: Versatility of glycals in synthetic organic chemistry: coupling reactions, diversity oriented synthesis and natural product synthesis

Back to tab navigation

Article information


Submitted
11 Feb 2019
Accepted
13 Mar 2019
First published
14 Mar 2019

Org. Biomol. Chem., 2019,17, 4153-4182
Article type
Review Article

Versatility of glycals in synthetic organic chemistry: coupling reactions, diversity oriented synthesis and natural product synthesis

H. H. Kinfe, Org. Biomol. Chem., 2019, 17, 4153
DOI: 10.1039/C9OB00343F

Social activity

Search articles by author

Spotlight

Advertisements