Issue 17, 2007
From the journal:

Organic & Biomolecular Chemistry

Enantiospecific synthesis of the heparanase inhibitor (+)-trachyspic acid and stereoisomers from a common precursor†

Steven C. Zammit,a   Vito Ferro,b   Edward Hammondb  and  Mark A. Rizzacasa*a  

* Corresponding authors

a School of Chemistry, Bio21 Institute, 30 Flemington Rd, The University of Melbourne, Victoria 3010, Australia
E-mail: masr@unimelb.edu.au
Fax: +61 3 9347 5180
Tel: +61 3 8344 2397

b Progen Pharmaceuticals Ltd, PO Box 2403, Toowong, Queensland 4066, Australia

Abstract

The total synthesis of natural (+)-trachyspic acid and its enantiomer is described starting from a common 2-deoxy-D-ribose derivative. The synthesis of the corresponding C3 epimers from the same starting material is also described. Each stereoisomer was assayed for heparanase inhibition.

Graphical abstract: Enantiospecific synthesis of the heparanase inhibitor (+)-trachyspic acid and stereoisomers from a common precursor

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Article information

DOI
https://doi.org/10.1039/B708594J
Article type
Paper
Submitted
06 Jun 2007
Accepted
20 Jun 2007
First published
26 Jul 2007

Org. Biomol. Chem., 2007,5, 2826-2834

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Enantiospecific synthesis of the heparanase inhibitor (+)-trachyspic acid and stereoisomers from a common precursor

S. C. Zammit, V. Ferro, E. Hammond and M. A. Rizzacasa, Org. Biomol. Chem., 2007, 5, 2826 DOI: 10.1039/B708594J

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