ORGN 747 |
Rhodexin A, the L-rhamnoside of sarmentogenin, is a cardiac glycoside that was isolated in 1951 from the leaves and roots of the evergreen Rhodea japonica. Rhodexin A is active against human leukemia K562 cells (IC50 19 nM). Like all cardiac glycosides, rhodexin A differs from most common steroids in that its AB and CD rings are cis rather than trans fused, and it possesses a tertiary hydroxyl group at C14 and a β-butenolide substituent at C17. A highly regio and stereoselective inverse-electron-demand Diels-Alder reaction was used to construct the BCD ring system of the steroid. The progress toward the total synthesis as well as the formation of the A ring and β-butenolide will be discussed. |
Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster
Division of Organic Chemistry |