The synthesis of the anti-malarial natural product polysphorin and analogues using polymer-supported reagents and scavengers.
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.
Lee
Ai-Lan
AL
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK CB2 1EW.
Ley
Steven V
SV
D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry; D001205:Ascorbic Acid / Q000737:chemistry; D016227:Benzoquinones / Q000494:pharmacology*; D001639:Bicarbonates / Q000737:chemistry; D002845:Chromatography; D006900:Hydroxylation; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D008049:Lipase / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008958:Models, Molecular; D010963:Plasmodium falciparum / Q000378:metabolism; D011108:Polymers / Q000737:chemistry*
D000962:Antimalarials; D016227:Benzoquinones; D001639:Bicarbonates; D017705:Lignans; D011108:Polymers; C491974:polysphorin; C000928:dichlorodicyanobenzoquinone; D008049:Lipase; D001205:Ascorbic Acid