Total synthesis of belactosin C and derivatives via double diastereoselective tandem Mukaiyama aldol-lactonizations

ORGN 120

Sung Wook Cho, scho@mail.chem.tamu.edu, Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, TX 77840 and Daniel Romo, romo@tamu.edu, Department of Chemistry, Texas A&M Univ, P.O. Box 30012, College Station, TX 77845.
The enantioselective synthesis of (-)-belactosin C and derivatives was accomplished in a concise manner employing the tandem, Mukaiyama aldol-lactonizaton (TMAL) process. One approach involved a distal double diastereoselective TMAL reaction with a dipeptide glyoxamide, whereas a second approach involved amide coupling of a dipeptide with a -lactone carboxylic acid, obtained via the TMAL process employing a chiral silyl ketene acetal. Notable improvements in diastereoselectivity were achieved in a proximal double diastereoselective TMAL process.

 

Total Synthesis, Materials, Devices and Switches, Molecular Recognition and Self-Assembly, Biologically-Related Molecules and Processes
8:00 PM-10:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007