Total synthesis of the antifungal natural product (-)-pramanicin

ORGN 736

Christopher G. Meyer, christgm@usc.edu, Cheol Hwan Yoon, cheolhwan.yoon@usc.edu, and Kyung Woon Jung, kwjung@usc.edu. Department of Chemistry, University of Southern California, Loker LHI 132, 837 Bloom Walk, Los Angeles, CA 90089
Progress towards the total synthesis of the antifungal natural product (-)-pramanicin is reported. This molecule consists of a functionalized lipophilic side chain bound to the 4-position of a chiral γ-lactam. The key steps involve (i) aldol reaction of an α,β-unsaturated, γ,δ-epoxy aldehyde with an α-diazoacetamide, (ii) Rh(II)-catalyzed intramolecular C-H insertion of the resultant diazo-aldol adduct, and (iii) stereoselective hydroxylation of the subsequent β-dicarbonyl array.

 

Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006