ORGN 225 |
| We have developed an epoxide-based methodology for the construction of polypropionates, consisting of a repetitive sequence of steps. Our approach involves a regioselective epoxide cleavage with an alkynyl alane reagent, reduction the alkyne, and the stereoselective epoxidation of the resulting alkene for the elaboration of each propionate unit. Our method usually relies on iodocyclization reactions for the epoxidation of homoallylic alcohols. However, these procedures do not produce all of the required 3,4-epoxy alcohols isomers. To overcome this limitation, we introduced an allylic alcohol into our homoallylic alcohol framework, using a functionalized alkynyl alane reagent. This modification allowed us to use peracids to perform an allylic controlled epoxidation procedure and facilitated the preparation of advanced propionate chains related to the synthesis of the elaiophylin polypropionate unit.
|
|
New Reactions and Methodology
1:00 PM-5:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- C301, Oral
Division of Organic Chemistry |
