ORGN 469 |
| Polypropionates are a common feature of many macrolide natural products. They consist of an array of alternating methyl and hydroxy groups on an aliphatic chain with a particular configuration. The challenges involving the synthesis of polypropionate units, particularly those in macrolides antibiotics, make them attractive synthetic targets. Our current synthetic efforts are focused on the synthesis of these units by means of an alkynyl or propenyl organometallic-assisted epoxide cleavage approach. Our multistep approach to polypropionates requires judicious selection and manipulation of protecting groups. Therefore, we have focused on trimethylsilylethoxymethyl, tert-butyldimethylsilyl and methoxyethoxymethyl protecting groups as alternatives, where other groups have presented lability or regioselectivity problems. To test the strength and efficacy of these protecting groups, we have performed a series of synthetic manipulations, which include epoxidations and epoxide cleavage, on our epoxy alcohol precursors. The results will be explained using molecular modeling where applicable. Work supported by NIH-SCORE (2S06GM-08102-29) |
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New Reactions and Methodology, Total Synthesis, Materials, Devices and Switches, Lipids, Nucleotides and Mimetics
8:00 PM-10:00 PM, Tuesday, March 27, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Organic Chemistry |