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Wednesday, April 26 • 2:40pm - 3:00pm
Synthesis of a Difluoro Combretastatin Analog

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Combretastatin A-4, an anti-tumor agent isolated from the Combretum caffrum bush, along with some synthetic derivatives, have been found to be effective in combating tumors by initiating vasculature collapse. While investigations into increasing combretastatins’ activity have focused mainly on utilizing a central ring to gain conformational locking have been performed, these modifications can have the undesired effect of creating a molecule too large or planar to attach to the corresponding binding site. This research focuses on bridge and b-ring fluorine substituted CA-4 derivatives to obtain the same desirable outcomes desired with CA-4, with the avoidance of steric hindrance. A total synthesis of an alpha, 3’-difluoro CA-4 analog was attempted with the use of diazonium salts in a Balz-Schiemann reaction using fluoride nucleophiles. However, a new pathway, using Duff formylation and the Wittig reaction to generate the B-ring, a Grignard reaction to synthesize the A-ring, and a final Suzuki coupling is being explored. The versatility of the diazonium salts are also being investigating for creating interesting heterocyclic molecules, namely tetrazoles, as well.

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Wednesday April 26, 2017 2:40pm - 3:00pm
123 Zeis Hall