Total synthesis of mycestericin A

Hideyuki Sato, Kazuya Sato, Masatoshi Iida, Hiroyoshi Yamanaka, Takeshi Oishi, Noritaka Chida

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The first total synthesis of mycestericin A (1) starting from tartrates is described. The Overman rearrangement of an allylic trichloroacetimidate generated a tetra-substituted carbon with nitrogen, and subsequent stereoselective transformations afforded the highly functionalized vinyl iodide. The cross-coupling of the vinyl iodide with a chiral organozinc species under Negishi conditions, followed by deprotection, completed the total synthesis of 1.

Original languageEnglish
Pages (from-to)1943-1947
Number of pages5
JournalTetrahedron Letters
Volume49
Issue number12
DOIs
Publication statusPublished - 2008 Mar 17

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Keywords

  • Immunosuppressant
  • Mycestericin A
  • Negishi coupling
  • Overman rearrangement
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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