An efficient and enantioselective total synthesis of naturally occurring L-783277

Naturally occurring L-783277 which belongs to 14-membered resorcylic acid lactones (RALs) turned out to be a potent kinase inhibitor against MEK (MAP kinase kinase). We successfully accomplished efficient and enantioselective total synthesis of L-783277 based on convergent assembly of one aromatic u...

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Bibliographic Details
Published in:Tetrahedron letters 2010-09, Vol.51 (38), p.4942-4946
Main Authors: Choi, Hwan Geun, Son, Jung Beom, Park, Dong-Sik, Ham, Young Jin, Hah, Jung-Mi, Sim, Taebo
Format: Article
Language:English
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Summary:Naturally occurring L-783277 which belongs to 14-membered resorcylic acid lactones (RALs) turned out to be a potent kinase inhibitor against MEK (MAP kinase kinase). We successfully accomplished efficient and enantioselective total synthesis of L-783277 based on convergent assembly of one aromatic unit and two chiral building blocks with efficient orthogonal protection-deprotection strategy. Three key steps composed of olefin cross metathesis, addition of acetylene derivative to aldehyde, and Yamaguchi macrolactonization were subsequently employed to construct the framework of L-783277. The optical rotation value of L-783277 is for the first time presented in this Letter.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.07.122