Convergent synthesis of macrolide core of (+) Migrastatin

ORGN 174

Javed Iqbal, javediqbaldrf@hotmail.com1, Saibaba Vobbalareddy, saibabav@drreddys.com1, K. Mukkanti, kmukkanti@rediffmail.com2, and Parthasarathi Das, parthads@yahoo.com1. (1) Discovery Chemistry, Discovery Research, Dr. Reddy's Laboratories Ltd, Bollaram Road, Miyapur, Hyderabad, 500 049, A.P, India, (2) Chemistry Division, Institute of Science &Technology, JNT University, JNTU, Kukatpally, Hyderabad, 500072, India
Macrolides remain as a good synthetic targets due to their structural diversities, biological activities and important medicinal properties. (+) Migrastatin (1), a novel macrolide natural product displays a significant inhibition on the migration of human tumor cells. The synthesis of the 14-membered macrolide core (3) of migrastatin envisaged the preparation of key intermediate (2) via a diastereoselective aldol condensation and exclusive (Z)-olefination. Yamaguchi esterification of key intermediate (2) followed by ring-closing metathesis (RCM) produced the macrolide 3.


New Reactions and Methodology, Materials, Total Synthesis, Process R&D
8:00 PM-10:00 PM, Sunday, 28 August 2005 Washington DC Convention Center -- Hall A, Poster

8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005