Chemo-enzymatic short-step total synthesis of symbioramide

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

doi:10.1016/j.tetlet.2005.03.093

Chemo-enzymatic short-step total synthesis of symbioramide

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

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

18 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 language	English
Pages (from-to)	3291-3295
Number of pages	5
Journal	Tetrahedron Letters
Volume	46
Issue number	19
DOIs	https://doi.org/10.1016/j.tetlet.2005.03.093
Publication status	Published - 2005 May 9

Keywords

Aminolysis
Dihydrosphingosine
Lipase
Symbioramide
α-Hydroxy acid

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.tetlet.2005.03.093

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title = "Chemo-enzymatic short-step total synthesis of symbioramide",

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.",

keywords = "Aminolysis, Dihydrosphingosine, Lipase, Symbioramide, α-Hydroxy acid",

author = "Tsukasa Takanami and Hiroki Tokoro and Kato, {Dai Ichiro} and Shigeru Nishiyama and Takeshi Sugai",

note = "Funding Information: We deeply thank Professor emeritus Kenji Mori, the University of Tokyo, for information and spectra on synthetic symbioramide and its diastereomer, and Amano Enzyme Inc. for lipase PS. This work was accomplished as the 21st Century COE Program (KEIO LCC), also supported by {\textquoteleft}SORST: Solution-Oriented Research for Science and Technology{\textquoteright} of Japan Science and Technology Corporation, and we express our sincere thanks to Professors Keisuke Suzuki, Takashi Matsumoto and Dr. Ken Ohmori of Tokyo Institute of Technology.",

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AU - Takanami, Tsukasa

AU - Tokoro, Hiroki

AU - Kato, Dai Ichiro

AU - Nishiyama, Shigeru

AU - Sugai, Takeshi

N1 - Funding Information: We deeply thank Professor emeritus Kenji Mori, the University of Tokyo, for information and spectra on synthetic symbioramide and its diastereomer, and Amano Enzyme Inc. for lipase PS. This work was accomplished as the 21st Century COE Program (KEIO LCC), also supported by ‘SORST: Solution-Oriented Research for Science and Technology’ of Japan Science and Technology Corporation, and we express our sincere thanks to Professors Keisuke Suzuki, Takashi Matsumoto and Dr. Ken Ohmori of Tokyo Institute of Technology.

PY - 2005/5/9

Y1 - 2005/5/9

N2 - 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.

AB - 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.

KW - Aminolysis

KW - Dihydrosphingosine

KW - Lipase

KW - Symbioramide

KW - α-Hydroxy acid

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Chemo-enzymatic short-step total synthesis of symbioramide

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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