ORGN 371 |
Studies directed toward the total synthesis of bistramide A
| Michael T. Crimmins and Amy C. DeBaillie. Department of Chemistry, University of North Carolina at Chapel Hill, Venable and Kenan Laboratories of Chemistry, CB# 3290, Chapel Hill, NC 27599 |
| Bistramide A is a member of a class of bioactive polyethers that were isolated from the marine ascidian Lissoclinum bistratum. The potent biological activity of the bistramides has inspired several synthetic and NMR studies that have determined the relative stereochemistry at carbons 6 through 34, while the relative stereochemistry at C39 remains undetermined. Our synthetic strategy relies on the use of a convergent three segment coupling approach, which highlights methodology developed in our laboratory. Specifically, the stereochemistry of the trans disubstituted tetrahydropyran ring has been set using a diastereoselective thiazolidinethione aldol, while the stereochemistry of the spiroketal moiety has been established with an asymmetric glycolate alkylation and a Brown crotylation. Progress toward the construction of the three key fragments and efforts toward their assembly will be presented. 
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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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