ORGN 742 |
| When cyclohexa-2,5-dienone monoketals were treated with the lithium dianion of ethyl 3-nitropropionate, [3.2.1] bicyclooctanones were generated in preparatively useful yields upon treatment with mild acid. One of these adducts was regioselectively acylated and subjected to an intramolecular Heck reaction, which established the spirooxindole. The overall strategy allows rapid access to a core possessing suitable functionality for a synthesis of gelsemine.
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Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
