ORGN 630 |
Application of 2,7-dioxa-bicyclo[2.2.1]heptan-5-ones in the synthesis of natural products
| Peter J. Mikochik and Jeffrey D. Winkler. Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104 |
| Tandem reactions in organic synthesis have proven to be very powerful processes for the formation of multiple carbon-carbon bonds in a single step, usually with very good stereo- and regiochemical specificity. Substituted 2,7-dioxa-bicyclo[2:2:1]heptan-5-ones have been prepared via a tandem carbene induced cyclization / 1,3-dipolar cycloaddition between diazo ketones and aldehydes in good yield and diastereoselectivity. Using these bicycles, ring opening can be affected by either Samarium(II) iodide or TFA to give access to a variety of interesting products, which can be applied to the syntheses of diverse naturally occurring structures such as bryostatin and calyculin A. 
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New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 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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