Chemo-enzymatic short-step total synthesis of symbioramide

Tsukasa Takanami, Hiroki Tokoro, Dai Ichiro Kato, Shigeru Nishiyama, Takeshi Sugai

研究成果: Article査読

18 被引用数 (Scopus)

抄録

A concise synthesis of symbioramide, a marine-origin ceramide from a common starting material, methyl (±)-trans-2,3-epoxyoctadecanoate, in a convergent manner was achieved. The key step is the direct lipase-catalyzed coupling reaction between methyl (2R,3E)-2-hydroxy-3-octadecenoate and non-protected (±)-erythro-dihydrosphingosine, giving natural (2S,3R,2′R)-symbioramide and its (2R,3S,2′R)-isomer in 38% and 37% yield, respectively. The optically active β,γ-unsaturated α-hydroxyester was prepared by Mg(ClO4)2-mediated isomerization of epoxide and the subsequent lipase PS-catalyzed kinetic resolution.

本文言語English
ページ(範囲)3291-3295
ページ数5
ジャーナルTetrahedron Letters
46
19
DOI
出版ステータスPublished - 2005 5月 9

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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