Lavendamycin analogs and the total synthesis of novel compounds

CHED 428

Greg Thomas Donald, gtdonald@bsu.edu, Department of Chemistry, Ball State University, 410 N. McKinley Ave. Apt. 101, Muncie, IN 47303
Lavendamycin is known to be a potent anti-tumor agent, which was first isolated from the fermentation broth of Streptomyces Lavendulae at the Bristol Myers Laboratory in 1981. The first proposed total synthesis of these compounds was a 20 step synthesis with an overall yield of about 5 to 6%, our research group has found a new route of synthesis with only 5 synthetic steps, and an overall yield of 33%.

The 7-N-Acetyllavendamycin analogues are highly toxic towards cancer cells such as rask which correlates to human cancers such as carcinomas of the lungs, colon and pancreas. Due to the potent and strong cytotoxicity of these Lavendamycins, they may one day be used to treat cancer patients.

In our research project we have been working to synthesize new derivatives of compounds possessing the Lavendamycin skeleton. We are presenting our new synthetic methodologies of Lavendamycin Derivatives. These derivatives are hoped to have different biological activities.