Issue 21, 2002

A flexible synthesis of cyclopentitol derivatives based on ring-closing metathesis of carbohydrate-derived 1,6-dienes

Abstract

Four partially protected stereoisomeric cyclopentenetriols 5, 10, 15 and 21 have been prepared by ring-closing metathesis of carbohydrate-derived 1,6-dienes. The presence of a differentiated allylic alcohol in the cyclopentenetriols allows a variety of synthetic transformations, underlining the synthetic use of the prepared cyclopentenetriol derivatives as chiral building blocks.

Graphical abstract: A flexible synthesis of cyclopentitol derivatives based on ring-closing metathesis of carbohydrate-derived 1,6-dienes

Article information

Article type
Paper
Submitted
01 Aug 2002
Accepted
09 Sep 2002
First published
08 Oct 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 2370-2377

A flexible synthesis of cyclopentitol derivatives based on ring-closing metathesis of carbohydrate-derived 1,6-dienes

H. Ovaa, B. Lastdrager, J. D. C. Codée, G. A. van der Marel, H. S. Overkleeft and J. H. van Boom, J. Chem. Soc., Perkin Trans. 1, 2002, 2370 DOI: 10.1039/B207509A

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