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

Ai-Lan Lee, Steven V. Ley

Research output: Contribution to journalArticlepeer-review

50 Citations (SciVal)

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.
Original languageEnglish
Pages (from-to)3957-3966
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume1
Issue number22
DOIs
Publication statusPublished - 2003

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