Progress towards the total syntheses of floresolides A and B

ORGN 566

Timothy F Briggs and Gregory B. Dudley. Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306
Progress towards the synthesis of floresolides A and B will be reported. Our strategy centers around a ring-expansion reaction to avoid the high entropic barrier for macrocyclization. We are investigating a tandem Claisen rearrangement/hemiketal-Grob fragmentation to synthesize the macrolide core. The preparation of the precursor 1 involves a diastereoconvergent 1,2-addition/hemiketalization, and subsequent reduction sets up the requisite stereochemistry for fragmentation.

 

Total Synthesis of Complex Molecules
1:00 PM-5:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- 201B, Oral

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004