Parallel synthesis of macrocycles using an Ugi-RCM strategy

ORGN 342

Luyi Guo, Guobin Miao, Vivek Joshi, Libing Yu, and Carmen M. Baldino. Department of Chemistry, ArQule, Inc, 19 Presidential Way, Woburn, MA 01801

A strategy for parallel synthesis of macrocycles coupling the Ugi reaction with olefin metathesis has been developed.  The Ugi reaction is a powerful multi-component reaction, which provides access to a significant number of novel compounds. When terminal alkenes were incorporated into two of either the acid, amine or aldehyde component, the resulting products were transformed into medium to large ring systems through intramolecular olefin metathesis promoted by Grubbs catalyst.  The reaction scope and the preparation of specific macrocycles will be described.

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