118106-53-9Relevant academic research and scientific papers
Chemo-enzymatic short-step total synthesis of symbioramide
Takanami, Tsukasa,Tokoro, Hiroki,Kato, Dai-Ichiro,Nishiyama, Shigeru,Sugai, Takeshi
, p. 3291 - 3295 (2005)
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.
Study of the Cross-Metathesis Reaction of α-Hydroxy β,γ-Unsaturated Amides towards a Rapid and Flexible Total Synthesis of Symbioramide and its Isomer
Gratais, Alexandre,Bouzbouz, Samir
supporting information, p. 230 - 234 (2018/03/26)
The reactivity of novel α-hydroxy β,γ-unsaturated amides in cross-metathesis reactions was extensively studied and used to perform a short total synthesis of symbioramide and its isomer from l -serine methyl ester.
Total synthesis of symbioramide: A flexible approach for the efficient preparation of structural isomers
Prevost, Sebastien,Ayad, Tahar,Phansavath, Phannarath,Ratovelomanana-Vidal, Virginie
experimental part, p. 3213 - 3226 (2012/01/03)
A concise, enantioselective total synthesis of symbioramide, starting from simple achiral compounds and racemic α-amino-β-keto ester derivatives is reported. This highly flexible strategy allowed the efficient preparation of seven structural isomers of the natural product as well. The synthesis relies on a convergent route that involves the efficient stereoselective reduction of a α-keto-β-yne ester, and the dynamic kinetic resolution of an α-amino-β-keto ester through ruthenium-mediated asymmetric hydrogenation. Copyright
Total syntheses of symbioramide derivatives from L-serine and their antileukemic activities
Azuma, Hideki,Takao, Ryoko,Niiro, Hayato,Shikata, Keiji,Tamagaki, Seizo,Tachibana, Taro,Ogino, Kenji
, p. 2790 - 2797 (2007/10/03)
Naturally occurring symbioramide, (2S,3R,2′R,3′E)-N-(2′-hydroxy-3′-octadecenoyl)- dihydrosphingosine 1a, was synthesized from D-erythro-dihydrosphingosine (amino part, 2) and (2R,3E)-2hydroxy-3-octadecenoic acid (acid part, 3a), both of which were prepared from L-serine. Its diastereomer, (2S,3R,2′S,3′E)-1b, having an enantiomer of the unnatural-type acid part that was prepared from D-mannitol, and its corresponding (Z)-isomers, (2S,3R,2′R,3′Z)-1c and (2S,3R,2′S,3′Z)1d, were also prepared. The antileukemic activities of 1a-d against HL-60 and L-1210 cells were appreciated by a MTT assay. None of the four symbioramide derivatives showed antileukemic activities in HL-60 cells. In L-1210 cells, all the symbioramide derivatives showed moderate antileukemic activities. Compound 1d had the most effective activity against L-1210 cells among the four derivatives. The data suggest that unnatural types of (2′S)-isomers of acid parts are more active than those of (2′R)-isomers.
Synthesis of Sphingosine Relatives, XIV. A New Synthesis of Symbioramide, a Ca(++)-ATPase Activator from Symbiodinium sp.
Mori, Kenji,Uenishi, Keiji
, p. 41 - 48 (2007/10/02)
Symbioramide was synthesized from D-erythro-dihydrosphingosine (19) and (R,E)-2'-tert-butyldimethylsilyloxy-3'-octadecenoic acid (14), which was prepared from (E)-2-octadecen-1-ol (4) by employing the Sharpless asymmetric epoxidation.The (2S,2'S,3R,3'E)-isomer 28 of 1 was also synthesized to further confirm the structure of 1. - Key Words: Ca(++)-ATPase activator / Ceramides / Marine natural products / Sphingosines / Symbioramide
Total Synthesis of Symbioramide, a Novel Ca(2+)-ATPase Activator from Symbiodinium sp.
Yoshida, Jun,Nakagawa, Masako,Seki, Hiroko,Hino, Tohru
, p. 343 - 350 (2007/10/02)
The first total synthesis of symbioramide 1 has been accomplished by the coupling of D-erythro-dihydrosphingosine with an unusual, chiral α-hydroxy-β,γ-unsaturated fatty acid prepared from L-ascorbic acid, and simultaneously established the complete stereostructure of 1 to be (2S,2'R,3R,3'E)-N-(2'-hydroxyoctadec-3'-enoyl)dihydrosphingosine.
First Total Synthesis of Symbioramide, a Novel Ca2+-ATPase Activator from Symbiodinium sp.
Nakagawa, Masako,Yoshida, Jun,Hino, Tohru
, p. 1407 - 1410 (2007/10/02)
The first total synthesis of symbioramide (1) is described and simultaneously established the complete stereostructure of 1 to be (2S,3R,2'R,3'E)-N-(2'-hydroxy-3'-octadecenoyl)-dihydrosphingosine.
