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

Hwan Geun Choi, Jung Beom Son, Dong Sik Park, Young Jin Ham, Jung Mi Hah, Taebo Sim

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)4942-4946
Number of pages5
JournalTetrahedron Letters
Volume51
Issue number38
DOIs
Publication statusPublished - 2010

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Choi, H. G., Son, J. B., Park, D. S., Ham, Y. J., Hah, J. M., & Sim, T. (2010). An efficient and enantioselective total synthesis of naturally occurring L-783277. Tetrahedron Letters, 51(38), 4942-4946. https://doi.org/10.1016/j.tetlet.2010.07.122