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Synthesis of the C1-C13 fragment of migrastatin

Ilton Barros Daltro de Castro
Total Authors: 1
Document type: Master's Dissertation
Institution: Universidade Estadual de Campinas (UNICAMP). Instituto de Química
Defense date:
Examining board members:
Silvio do Desterro Cunha; Fernando Antonio Santos Coelho
Advisor: Luiz Carlos Dias

Migrastatin was isolated from a cultured broth of Streptomyces sp. MK929-43F1 in 2000 by Imoto and co-workers, as well as from a cultured broth of Streptomyces platensis NRRL 18993 by researchers from Kosan Biosciences. Migrastatin has a remarkable inhibitory effect on the migration of human tumor cells, very important to the tumor metastasis treatment. Its relative stereochemistry and absolute configurations were determined by X-ray analysis of a derivative. Migrastatin is a 14-membered lactone with a glutarimide side chain, 5 stereogenic centers and 3 double bonds. We wish to describe here an approach to the C1-C13 fragment of migrastatin. The key steps for the construction of the C1-C13 fragment of migrastatin are: a syn-aldol reaction to set up the C9 and C10 stereogenic centers, followed by a (Z)-seletive Horner-Wadsworth-Emmons reaction and esterification of carboxilic acid 65 (fragment C1-C6) with allylic alcohol 66 (fragment C8-C13) (AU)