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):

Report Date:

1990-02-23

Pagination or Media Count:

16.0

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

Subject Categories:

  • Pharmacology

Distribution Statement:

APPROVED FOR PUBLIC RELEASE