ORGN 482 |
| Leland O. Weigel1, John A. Werner1, Joseph H. Kennedy2, and Perry C. Heath1. (1) Chemical Process Development and Commercialization, Lilly Research Laboratories - A Division of Eli Lilly & Company, Lilly Technology Center South, Indianapolis, IN 46254-4813, (2) Discovery Chemistry Research & Technologies, Eli Lilly and Company, Lilly Research Labs, Indianapolis, IN 46285 |
| As part of a program to support an SAR of potential b-3 agonist drug candidates, we required a general route for the conversion of 4-hydroxyl substituted indoles and carbazoles (1) into the corresponding non-racemic epoxides (4, n=0, 1, 2) and then into targets (5, n=0, 1, 2). We employed the Sharpless asymmetric dihydroxylation (AD) reaction with the corresponding terminal olefin (2) to produce diol 3 followed by tin-catalyzed monotosylation and closure to non-racemic epoxide (4, n=0, 1, 2). We shall describe and discuss the methods used to prepare the olefins (2), chiral chromatographic separations of 3 (n=0, 1, 2) and the enantioselectivity of the AD in this series. |
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Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster
Division of Organic Chemistry |
