title: Enantioselective synthesis of sphingadienines and aromatic ceramide analogs.
abstract: A new approach to the synthesis of sphingoid bases has been developed. The strategy is based on Sonogashira coupling of a chiral acetylenic carbamate that can be prepared in enantiomerically enriched form from 2,3-epoxy-4-pentyn-1-ol, which is readily accessible by Sharpless asymmetric epoxidation. Several N-Boc-sphingadienines and aromatic ceramide analogs have been synthesized.
authors: Unitat de Recerca en Síntesi Asimètrica (URSA-PCB), Institute for Research in Biomedicine (IRB) and Departament de Química Orgànica, Universitat de Barcelona, c/Baldiri Reixac, 10, E-08028 Barcelona, Spain.
authors: María
authors: M
authors: Moreno
authors: Caterina
authors: C
authors: Murruzzu
authors: Antoni
authors: A
authors: Riera
mesh_terms: D002219:Carbamates / Q000737:chemistry; D002518:Ceramides / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry; D004983:Ethanolamines / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
chemical_list: D002219:Carbamates; D002518:Ceramides; D004852:Epoxy Compounds; D004983:Ethanolamines; D014753:Vinyl Compounds; C003337:sphingadienine