ORGN 133 |
One-pot Zr-catalyzed asymmetric carboalumination- Pd-catalyzed cross-coupling tandem process: Its application to the syntheses of siphonarienes and borrelidin
| Tibor Novak and Ei ichi Negishi. Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907-2084 |
| Zr-Catalyzed asymmetric carboalumination of alkenes is a useful method for the synthesis of reduced polypropionates which are common synthons for numerous natural products. We describe the results obtained in the development of a highly satisfactory one-step iterative method for the synthesis of reduced polypropionates. Our one-pot iterative protocol consisting of (i) Zr-catalyzed asymmetric carboalumination of an alkene, (ii) transmetalation, and (iii) Pd-catalyzed vinylation is efficient and generally applicable to the synthesis of reduced polypropionates containing 2 or more branching methyl groups. The synthetic use of this new method has been demonstrated by preparing an intermediate for the synthesis of borrelidin and the key intermediate for the syntheses of siphonarienes. 
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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