Stereoselective Total Synthesis of Radiolabeled Artemisinin (Qinghaosu).
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)
Document Details
- Document Type
- Technical Report
- Publication Date
- Feb 23, 1990
- Accession Number
- ADB142032
Entities
People
- Mitchell A. Avery
Organizations
- SRI International