150990-67-3Relevant articles and documents
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 (1995)
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.
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.
METHOD FOR DETERMINATION OF ENANTIOMERIC COMPOSITION AND ABSOLUTE CONFIGURATION OF 2,3-DEUTERATED 3-ALKYLPROPANOLS
Furukawa, Jun,Iwasaki, Shigeo,Okuda, Shigenobu
, p. 5257 - 5260 (2007/10/02)
Assignments were made for diastereotopic methylene protons on C-2 and C-3 of 1-phenyl-3-alkylpropanols in Eu(fod)3-enhanced 1H-NMR spectra to develope a generally applicable method to determine enantiomeric composition and absolute configuration of 2 and/or 3-deuterated 3-alkylpropanols.