Total synthesis of piperidine based alkaloids using a chiral non-racemic oxo-dihydropyridinyl molybdenum complex as a common scaffold

ORGN 73

Heilam Wong, hwong2@emory.edu and Lanny S. Liebeskind. Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, GA 30322
The oxo-dihydropyridinyl molybdenum complex 1 was synthesized and resolved through a highly efficient sequence in large quantity. Through five steps of stereocontrolled transformations, the 2, 3, and 6 positions of 1 were functionalized affording complex 2 in high yield. Empolying different demetallation protocols, the trisubstituted piperidines 3 and 4 have been synthesized stereoselectively. The applications of this methodology in the total synthesis of indolizidine 209I and the first total synthesis of indolizidine 219F will be discussed.

 

Asymmetric Reactions and Syntheses
1:00 PM-5:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- C302, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006