Total synthesis of mycestericin A and its 14-epimer

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

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

The total synthesis of mycestericin A (1) and its 14-epimer 34 is described herein. The Overman rearrangement of an allylic trichloroacetimidate derived from l-tartrate generated a tetra-substituted carbon with nitrogen and subsequent stereoselective transformations afforded the highly functionalized left-half segment, vinyl iodide. Cross-coupling of the vinyl iodide with a chiral organometallic species synthesized from d-tartrate under the Negishi or Suzuki-Miyaura coupling conditions, followed by deprotection, completed the total synthesis of 1. The 14-epimer of mycestericin A was also synthesized, and a comparison of [α]D values of peracetyl γ-lactone derivatives of mycestericin A and its 14-epimer as well as degradation studies of 1 and 34 fully confirmed the proposed absolute structure of mycestericin A.

Original languageEnglish
Pages (from-to)9188-9201
Number of pages14
JournalTetrahedron
Volume65
Issue number45
DOIs
Publication statusPublished - 2009 Nov 7

Fingerprint

Organometallics
Lactones
Nitrogen
Carbon
Derivatives
Degradation
mycestericin A
tartaric acid
vinyl iodide
trichloroacetamide

Keywords

  • Mycestericin A
  • Negishi coupling
  • Overman rearrangement
  • Suzuki-Miyaura coupling
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Total synthesis of mycestericin A and its 14-epimer. / Yamanaka, Hiroyoshi; Sato, Kazuya; Sato, Hideyuki; Iida, Masatoshi; Oishi, Takeshi; Chida, Noritaka.

In: Tetrahedron, Vol. 65, No. 45, 07.11.2009, p. 9188-9201.

Research output: Contribution to journalArticle

Yamanaka, H, Sato, K, Sato, H, Iida, M, Oishi, T & Chida, N 2009, 'Total synthesis of mycestericin A and its 14-epimer', Tetrahedron, vol. 65, no. 45, pp. 9188-9201. https://doi.org/10.1016/j.tet.2009.09.012
Yamanaka, Hiroyoshi ; Sato, Kazuya ; Sato, Hideyuki ; Iida, Masatoshi ; Oishi, Takeshi ; Chida, Noritaka. / Total synthesis of mycestericin A and its 14-epimer. In: Tetrahedron. 2009 ; Vol. 65, No. 45. pp. 9188-9201.
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