ORGN 369 |
Application of [3+2] annulation reactions of chiral allylsilanes and chiral aldehydes in the total synthesis of annonaceous acetogenins
| William R. Roush, Eric Mertz, and Jennifer M. Tinsley. Department of Chemistry, University of Michigan, 930 N. University Ave., Ann Arbor, MI 48109-1055 |
| The annonaceous acetogenins are a large, structurally diverse class of fatty acid derived natural products with impressive anti-tumor and insecticidal properties. Several of the most potent annonaceous acetogenins possess two adjacent tetrahydrofuran rings, but the stereochemistry of the bis-tetrahydrofuran core unit differs among many of the natural products. A synthesis of the bis-tetrahydrofuran annonaceous acetogenin asimicin has been accomplished by two successive [3+2] annulation reactions of chiral beta-silyloxy allylsilanes. Application of the [3+2] annulation methodology towards the synthesis of other, stereochemically distinct annonaceous acetogenins has been undertaken. Towards this end, several bis-tetrahydrofuran core structures have been synthesized, including one possessing the threo-cis-erythro-trans-threo relative configuration found in 10-hydroxytrilobacin. Progress towards completion of the total synthesis of 10-hydroxytrilobacin will presented, and elaboration of the [3+2] annulation approach towards the total synthesis of bullatacin and rollimembrin will also be discussed. 
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Total Synthesis, Process R&D, Combinatorial, Bioorganic, Physical Organic Chemistry
8:00 PM-10:00 PM, Tuesday, August 24, 2004 Pennsylvania Convention Center -- Hall D, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- Hall D, Sci-Mix
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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