ORGN 596 |
| Lasonolide A (1) is a potent cytotoxin against several cancer cell lines. This macrolide is a potent growth inhibitor against A-549 (human lung carcinoma) and P388 (murine leukemia) and also inhibits cell adhesion in the EL-4.IL-2 cell line. A series of studies including biological assays of numerous analogues showed that the levorotatory compound is the biologically active enantiomer. Additional structure-activity relationship studies showed that the cis double bond on the side chain is essential for the biological activity, which is further enhanced with the (R) configuration at C28. The structure of the 20-membered macroclide encloses two substituted tetrahydropyran fragments, one of which is penta-substituted including one quaternary carbon atom. We utilize the highly stereoselective Prins cyclization in our synthesis of the substituted tetrahydropyran fragments.
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New Reactions, Methodology, Total Synthesis, Physical Organic Chemistry
8:00 PM-10:00 PM, Tuesday, 15 March 2005 Convention Center -- Sails Pavilion, Poster
Sci-Mix
Division of Organic Chemistry |
