Total synthesis of mycestericin A and its 14-epimer

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

研究成果: Article査読

29 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)9188-9201
ページ数14
ジャーナルTetrahedron
65
45
DOI
出版ステータスPublished - 2009 11月 7

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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