ORGN 522 |
| We previously described a catalytic, asymmetric intramolecular nucleophile, catalyzed aldol-lactonization (NCAL) process employing aldehyde-acid substrates that effectively merges catalytic asymmetric carbocycle construction with ß-lactone synthesis (J. Am. Chem. Soc. 2001, 123, 7945). We have now expanded this process to allow the use of more tractable keto-acid substrates. This methodology enables a highly diastereoselective route to bicyclic and tricyclic ß-lactones bearing tertiary carbinol centers. The utility of this process was demonstrated by application to an enantioselective synthesis of dihydroplakevulin A, a derivative of the marine- derived DNA polymerase inhibitor, plakevulin. The derived carbocycle-fused ß-lactones should prove useful for applications in natural product and diversity-oriented synthesis.
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New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
