ORGN 632 |
Intramolecular reiterative silylformylation of diynes: A new methodology towards the synthesis of poly-oxygenated compounds
| Greta Varchi and Iwao Ojima. Department of Chemistry, State University of New York at Stony Brook, Stony Brook, NY 11794-3400 |
| We report here an application of reiterative silylformylation of siloxyalkynes for the synthesis of poly-oxygenated compounds. The silylformylation of 4-siloxydiyne 1 catalyzed by Rh(acac)(CO)2 under CO atmosphere gave the corresponding 5-exo-(formylmethylene)-oxasilacyclopentane 2. Reduction of 2 followed by Tamao oxidation and acetylation gave 3. Propargyl magnesium bromide addition followed by silylation afforded the siloxydiyne 4, which under the silylformylation conditions provided the bis oxasilacyclopentane 5. Compound 5 was subjected to the reduction-oxidation-acetylation sequence to yield highly functionalized product 6. Compounds 5 and 6 would serve as versatile intermediate for the synthesis of a variety of poly-oxygenated compounds. The isolated acetylene moiety turned out to be totally unaffected during those transformations, and can be used for further functionalizations. 
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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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