Accession Number : ADB142032
Title : Stereoselective Total Synthesis of Radiolabeled Artemisinin (Qinghaosu).
Descriptive Note : Final rept. 15 Nov 87-14 Jun 89,
Corporate Author : SRI INTERNATIONAL MENLO PARK CA
Personal Author(s) : Avery, Mitchell A.
Report Date : 23 FEB 1990
Pagination or Media Count : 16
Abstract : Our previous total synthesis of (+)-artemisinin has been optimized from 18 to 11 steps. The final two steps in the sequence are: 1) alkylation of a carboxylic acid dianion with methyl iodide, and 2) ozonolysis of a vinyl-silane followed by in situ acid-catalyzed cyclization to provide the natural product (+)-artemisinin. The first step was repeated utilizing carbon-14 methyl iodide and the sequence completed as before to afford the desired carbon-14labeled (+)-artemisinin. The label resides in the methyl group pendant from the lactone ring (ring D), the position of attachment being C-9, the carbon atom being C-16. Keywords: Antimalarials. (aw)
Descriptors : *ANTIMALARIALS, *ANTIMALARIALS, ALKYLATION, ATOMS, ATTACHMENT, CARBON, IODIDES, METHYL RADICALS, POSITION(LOCATION).
Subject Categories : Pharmacology
Distribution Statement : APPROVED FOR PUBLIC RELEASE