Chemo-enzymatic short-step total synthesis of symbioramide

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

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3291-3295
Number of pages5
JournalTetrahedron Letters
Volume46
Issue number19
DOIs
Publication statusPublished - 2005 May 9

Keywords

  • Aminolysis
  • Dihydrosphingosine
  • Lipase
  • Symbioramide
  • α-Hydroxy acid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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