@article{51cac98356b647eeaffa9fce844c8a8d,
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.",
year = "2005",
month = may,
day = "9",
doi = "10.1016/j.tetlet.2005.03.093",
language = "English",
volume = "46",
pages = "3291--3295",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "19",
}
