ORGN 592 |
Synthesis of enantiopure dihydropyranones: Aldol-based ring expansion of dihydrofurans
| Graeme C. Freestone and Timothy J. Donohoe. Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, United Kingdom |
We have developed a stereoselective Birch reduction of 3-methyl-2-furoic acids using a readily available chiral auxiliary; by coupling this process to an oxidative cleavage/aldol ring closure sequence we were able to produce highly functionalized and enantiopure dihydropyranones in high yield. This sequence has ample flexibility built into it, either by the use of different electrophiles during reductive alkylation or by subsequent derivatization of the dihydropyranone after ring expansion. |
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Bioorganic, Molecular Recognition, Asymmetric Reactions and Syntheses
11:00 AM-1:00 PM, Wednesday, September 10, 2003 Javits Convention Center -- Hall 1B/1C, Poster
Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003
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