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

Fingerprint

Tartrates
Nitrogen
Carbon
mycestericin A
vinyl iodide
trichloroacetamide

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Total synthesis of mycestericin A. / Sato, Hideyuki; Sato, Kazuya; Iida, Masatoshi; Yamanaka, Hiroyoshi; Oishi, Takeshi; Chida, Noritaka.

In: Tetrahedron Letters, Vol. 49, No. 12, 17.03.2008, p. 1943-1947.

Research output: Contribution to journalArticle

Sato, H, Sato, K, Iida, M, Yamanaka, H, Oishi, T & Chida, N 2008, 'Total synthesis of mycestericin A', Tetrahedron Letters, vol. 49, no. 12, pp. 1943-1947. https://doi.org/10.1016/j.tetlet.2008.01.105
Sato, Hideyuki ; Sato, Kazuya ; Iida, Masatoshi ; Yamanaka, Hiroyoshi ; Oishi, Takeshi ; Chida, Noritaka. / Total synthesis of mycestericin A. In: Tetrahedron Letters. 2008 ; Vol. 49, No. 12. pp. 1943-1947.
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