Studies towards the total synthesis of (-) Borrelidin: Strategies for the C11-C15 fragment construction and the utility of RCM reaction for macrolide cyclization using model systems

ORGN 165

Vamsee K. Chintakunta, VAMSEEKRISHNA1@REDIFFMAIL.COM1, Santanu Maitra, santanumaitra@drreddys.com1, K. Mukkanti, kmukkanti@rediffmail.com2, and Javed Iqbal, javediqbaldrf@hotmail.com3. (1) Discovery Chemistry, Discovery Research, Dr. Reddy's Laboratories, Ltd, Bollaram Road, Miyapur, Hyderabad, 500049, India, (2) Chemistry Division, Institute of Science &Technology, JNT University, JNTU, Kukatpally, Hyderabad, 500072, India, (3) Discovery Research, Dr. Reddy's Laboratories Ltd, Bollaram Road, Miyapur, Hyderabad, 500049, India
Borrelidin was first isolated from Streptomyces rochei in 1949 by Jampolsky and Goldberg. Borrelidin exhibits a broad antiviral, antibacterial, antiangiogenic and antimitotic properties. The combination of an unusual chemical structure and a diverse biological profile has led to several synthetic routes for the synthesis of this macrolide. As part of our endeavor to synthesize this complex macrolide, we present here our strategies towards the synthesis of the C11-C15 conjugated cyanodiene synthon and demonstrate the utility of the ring closing metathesis reaction for the final macro cycle construction by using appropriate model systems.

 

Asymmetric Reactions and Syntheses, Physical Organic Chemistry, Combinatorial Chemistry, Total Synthesis
8:00 PM-10:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006