Asymmetric Michael addition of lithium propionate enolates to α, β unsaturated esters toward the total synthesis of Ionomycin A

ORGN 597

Sunjin Jo, sjo@chem.fsu.edu and Robert A. Holton. Department of chemistry and biochemistry, Florida State University, tallahassee, FL 32306
Lonomycin A, which was isolated from Streptomyces ribosidificus in 1975, is a polycyclic ether constituted of 6 highly functionalized rings and 23 stereocenters. Our synthetic strategy rely on the asymmetric Michael additions of propionate enolates to α, β unsaturated esters to introduce stereoselectively the contiguous and alternating methyl and methoxy moieties. This attractive methodology avoids the use of tedious protection-deprotection protocols and gives easily access to crucial intermediates in our synthetic approach.

 

Asymmetric Reactions and Syntheses
1:00 PM-5:00 PM, Wednesday, March 28, 2007 McCormick Place Lakeside -- Room E351, Level 3, Oral

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007