Synthesis of a cofacial porphyrenediyne and studies toward facilitated Bergman cyclization

CHED 886

John D. Spence and Hannah L. Heilveil. Department of Chemistry, Trinity University, One Trinity Place, San Antonio, TX 78212-7200
Enediyne antitumor antibiotics are a class of natural products that cleave DNA through 1,4-benzene diradicals formed upon Bergman cyclization of the enediyne unit. The synthesis and characterization of a cofacial diporphyrenediyne hybrid 1, in which the porphyrins are attached to the enediyne through their meso positions, has been achieved. The cofacial diporphyrin provides the opportunity to facilitate Bergman cyclization of the enediyne by introduction of a µ-oxo bridge between the two macrocycles as in compound 2. Studies into the synthesis and Bergman cyclization of 2 are currently in progress.

 

Undergraduate Research Poster Session: Organic Chemistry
2:00 PM-4:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Poster

Division of Chemical Education

The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004