ORGN 2 |
| A new strategy for the total synthesis of polyene-containing natural products is detailed and involved retrosynthetic excision of a 1,3-butadiene fragment from a polyene target. In this strategy, the 1,3-butadiene was differentially metallated with tin and boron at its termini, with the expectation that reaction conditions could be developed for orthogonal palladium-catalyzed cross-coupling with vinyl halides. Thus, the hetero-bis-metallaed butadiene could be interpolated within the polyene chain via a linchpin coupling by sequential Stille and Suzuki-Miyaura cross-coupling reactions. The application of this synthetic strategy to the total synthesis of the natural products lucilactaene, strobilurin B, and (6E)-O-methylmyxalamide D will be presented.
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Ernest Guenther Award in the Chemistry of Natural Products: Symposium in Honor of Dale L. Boger
8:45 AM-11:50 AM, Sunday, March 25, 2007 McCormick Place Lakeside -- Room E450 A/B, Level 4, Oral
Division of Organic Chemistry |
