Chemo-enzymatic short-step total synthesis of symbioramide

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

Research output: Contribution to journalArticle

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

Fingerprint

Lipase
Ceramides
Epoxy Compounds
Isomerization
Isomers
Kinetics
symbioramide
perchlorate
erythro-dihydrosphingosine

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Chemo-enzymatic short-step total synthesis of symbioramide. / Takanami, Tsukasa; Tokoro, Hiroki; Kato, Dai Ichiro; Nishiyama, Shigeru; Sugai, Takeshi.

In: Tetrahedron Letters, Vol. 46, No. 19, 09.05.2005, p. 3291-3295.

Research output: Contribution to journalArticle

Takanami, T, Tokoro, H, Kato, DI, Nishiyama, S & Sugai, T 2005, 'Chemo-enzymatic short-step total synthesis of symbioramide', Tetrahedron Letters, vol. 46, no. 19, pp. 3291-3295. https://doi.org/10.1016/j.tetlet.2005.03.093
Takanami, Tsukasa ; Tokoro, Hiroki ; Kato, Dai Ichiro ; Nishiyama, Shigeru ; Sugai, Takeshi. / Chemo-enzymatic short-step total synthesis of symbioramide. In: Tetrahedron Letters. 2005 ; Vol. 46, No. 19. pp. 3291-3295.
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