ORGN 476 |
Studies toward the synthesis of elaiophylin using epoxide cleavage
| Wilnelia Dávila and Jose A. Prieto. Department of Chemistry, University of Puerto Rico, PO Box 23346, San Juan, PR 00931-3346 |
| Elaiophylin is a C2 symmetric macrolide that exhibits antimicrobial activity against Gram-positive bacteria. Its structure contains a macrodiolide core and a polypropionate subunit. Polypropionates have attracted great interest due to its challenging structural array. We have developed a methodology for polypropionates synthesis using alkynyl alane reagents for the regioselective opening of 3,4-epoxy alcohols. After reduction of alkynyl moiety, the resulting cis or trans geometry of the alkene controls the configuration of the methyl groups, while the stereoselective epoxidation of the homoallylic alcohol introduces the configuration of the hydroxy groups. The synthetic studies using this methodology toward the construction of fragments 1 and 2 will be presented. Also the stereoselective epoxidations and preparation of elaiophylin monomeric fragment C4-C16 will be discussed. Supported by NIH SCORE (2S6GM-08102-29) and NIH RISE (1R25-GM-61151-01A1).  |
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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
Sci-Mix
8:00 PM-10:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Sci-Mix
Division of Organic Chemistry
The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004
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