News & Events

Dr. Herman Holt Jr.

Posted on February 13, 2015


Date - February 13, 2015
1:00 pm - 2:00 pm


Associate Professor of Chemistry
Chair, Department of Chemistry
UNC Asheville

“Synthesis of Heterocyclic Combretastatin and Chalcone Molecules”


Our group has set out to prepare indole analogues of combretastatin A-4 (CA-4) and chalcones.  Both CA-4 and some chalcones are effective tubulin binding agents which ultimately disrupts vascular function.   The Hemetsberger-Knittel method was used to successfully prepare substituted indoles from α-azidocinnamates in good yields.  Oxidation state adjustment generated a highly diverse indole aldehyde that can be used in a variety of ways.  One carbon homologation provided ethynyl indoles as functional dipolarophiles in catalyzed 1,3-dipolar cycloadditions to produce a 2-(1,2,3-triazolyl)indole.  In addition, the synthesis of indole chalcone and α-halo substituted indole analogs of CA-4 can be performed.  The synthesis of some indole aldehydes and their utility will be described in the seminar.