165880-19-3Relevant academic research and scientific papers
Synthesis of 6-Hydroxysphingosine and α-Hydroxy Ceramide Using a Cross-Metathesis Strategy
Wisse, Patrick,De Geus, Mark A. R.,Cross, Gen,Van Den Nieuwendijk, Adrianus M. C. H.,Van Rooden, Eva J.,Van Den Berg, Richard J. B. H. N.,Aerts, Johannes M. F. G.,Van Der Marel, Gijsbert A.,Codée, Jeroen D. C.,Overkleeft, Herman S.
, p. 7258 - 7265 (2015/07/27)
(Chemical Equation Presented) In this paper, a new synthetic route toward 6-hydroxysphingosine and α-hydroxy ceramide is described. The synthesis employs a cross-metathesis to unite a sphingosine head allylic alcohol with a long-chain fatty acid alkene that also bears an allylic alcohol group. To allow for a productive CM coupling, the sphingosine head allylic alcohol was protected with a cyclic carbonate moiety and a reactive CM catalyst system, consisting of Grubbs II catalyst and CuI, was employed.
The first total synthesis of the 6-hydroxy-4E-sphingenines
Yadav,Geetha,Raju, A. Krishnam,Gnaneshwar,Chandrasekhar
, p. 2983 - 2985 (2007/10/03)
Ceramides containing the 6-hydroxy-4E-sphingenines, previously unknown long-chain bases, have recently been found in human skin. A total synthesis of 6-hydroxy-4E-sphingenines has been achieved.
Electrophilic selenocyclization in 2-ene-1,5-diol systems: Unexpected oxetane vs. tetrahydrofuran formation
Van De Weghe, Pierre,Bourg, Stéphane,Eustache, Jacques
, p. 7365 - 7376 (2007/10/03)
Electrophile-induced cyclization of (E)- and (Z)-2-ene-1,5-diols to tetrahydrofurans and oxetanes is described. Significant differences between the present report and previous work have been noted. A tentative model is proposed.
Synthesis of (4R,5R)-Muricatacin and its (4R,5S)-Analog by Sequential Use of the Photo-Induced Rearrangement of Epoxy Diazomethyl Ketones
Aar, Marcel P. M. van,Thijs, Lambertus,Zwanenburg, Binne
, p. 11223 - 11234 (2007/10/02)
The naturally occuring δ-hydroxy-γ-lactone (4R,5R)-muricatacin and its nonnatural (4R,5S)-analog are synthesized.The starting achiral allylic alcohols are converted into α,β-epoxy diazomethyl ketones followed by a stereospecific irradiation reaction of these compounds to give 4-hydroxy-2-alkene esters.Using this method in a sequential manner a successive introduction of stereogenic centers is realized, resulting in enantiopure 4,5-dihydroxy-2-alkene esters.These alcohols are converted into the δ-hydroxy-γ-lactone muricatacin.
C-1 Reactivity of 2,3-Epoxy Alcohols via Oxirane Opening with Metal Halides: Application and Synthesis of Naturally Occuring 2,3-Octanediol, Muricatacin, 3-Octanol, and 4-Dodecanolide
Bonini, Carlo,Federici, Chiara,Rossi, Leucio,Righi, Giuliana
, p. 4803 - 4812 (2007/10/02)
The C-1 reactivity of 2,3-epoxy alcohols and derivatives has been examined thoroughly.In the first approach a rearrangement opening of 2,3-epoxy alcohols with LiI leads to 1-iodo 2,3-diols with erythro or threo stereochemistry starting from trans or cis epoxy alcohols.Subsequent coupling with a carbon nucleophile can lead to a series of vicinal diols with predicted relative and absolute stereochemistry: the described methodology has been applied to the asymmetric synthesis of the naturally occuring (S,S)-2,3-octanediol and (R,R)-muricatacin.The second approach, starting from easily available tosyloxy epoxides, leads to the highly regioselective opening of the oxirane ring with Li halides.The 3-iodohydrins obtained can be reduced to the corresponding 1-(tosyloxy)alkan-2-ols and then coupled with common carbon nucleophiles to afford, in high yields, optically active alcohols.This methodology has been applied to the asymmetric synthesis of naturally occuring pheromones like 3(R)-octanol and 4(R)-dodecanolide.
