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