Issue 22, 2003
From the journal:

Organic & Biomolecular Chemistry

The synthesis of the anti-malarial natural product polysphorin and analogues using polymer-supported reagents and scavengers

Ai-Lan Leea  and  Steven V. Ley*a  

* Corresponding authors

a Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK
E-mail: svl1000@cam.ac.uk
Fax: +44 (0) 1223 336442
Tel: +44 (0) 1223 336398

Abstract

A general asymmetric route to both enantiomers of polysphorin has been developed. The route utilizes polymer-supported reagents, catalysts and scavengers to minimise the need for aqueous work-up and chromatography. This includes application of a method to scavenge 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and a “catch-and-release” procedure to extract the resultant diol following Sharpless asymmetric dihydroxylation. A novel enzymatic selective protection and investigations of a new asymmetric dihydroxylation using microencapsulated osmium tetroxide were also investigated during the course of this study.

Graphical abstract: The synthesis of the anti-malarial natural product polysphorin and analogues using polymer-supported reagents and scavengers

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Article information

DOI
https://doi.org/10.1039/B308761A
Article type
Paper
Submitted
28 Jul 2003
Accepted
08 Sep 2003
First published
08 Oct 2003

Org. Biomol. Chem., 2003,1, 3957-3966

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The synthesis of the anti-malarial natural product polysphorin and analogues using polymer-supported reagents and scavengers

A. Lee and S. V. Ley, Org. Biomol. Chem., 2003, 1, 3957 DOI: 10.1039/B308761A

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