Progress towards the total synthesis of celogentin C

ORGN 735

Joshua S. Grimley, grimley@stanford.edu, Department of Chemistry, Stanford University, Clark Center W300, 318 Campus Drive, Stanford, CA 94305-5441 and Thomas J. Wandless, wandless@stanford.edu, Department of Molecular Pharmacology, Stanford University, Clark Center W350A, 318 Campus Drive, Stanford, CA 94305-5441.
Our studies en route to the synthesis of the antimitotic agent celogentin C will be presented. This bicyclic octapeptide contains novel Leu-Trp-His sidechain connections. We use Larock's indole methodology to construct the tryptophan residue. A nickel-mediated reaction couples a 2-iodoindole to a suitably protected histidine. Current studies include the synthesis of the Larock precursor, an aryl-substituted leucine residue.

 

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