Synthesis of the northern fragment of TMC-95A

ORGN 463

Ahalya Ramanathan, ahalya@eden.rutgers.edu and Leslie S. Jimenez. Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, NJ 08854
An oxidized tryptophan is a key component of the proteosome inhibitor, TMC-95A. Starting with N-Boc-L-tryptophan, the highly oxidized tryptophan derivative (TMC-95A northern fragment) was synthesized in 7 steps. A chloro group was introduced at the C-7 position of the oxindole sidechain with the aid of a blocking group at the C-5 position.
 

Total Synthesis of Complex Molecules
8:00 AM-12:00 PM, Wednesday, April 9, 2008 Morial Convention Center -- Rm. R05, Oral

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008