title: High-yielding synthesis of sphingoid-type bases.
abstract: An efficient methodology for the synthesis of sphingoid-type bases is reported. It involves the stereoselective addition of a racemic 3-alkoxy allenylzinc to enantiopure N-tert-butylsulfinyl imines and a cross-metathesis reaction as the key steps. It has been successfully applied to the syntheses of sphinganine and naturally occurring bioactive related compounds, among which the hydrolysis product of clavaminol H and two spisulosines. All of these compounds have been prepared in six steps from N-tert-butylsulfinyl imines in high overall yields (>56%).
authors: UPMC-Univ Paris 06, CNRS UMR 7201, Institut Parisien de Chimie Moléculaire (FR 2769), case 183, 4 place Jussieu, F-75005 Paris, France.
authors: Catherine
authors: C
authors: Séguin
authors: Franck
authors: F
authors: Ferreira
authors: Candice
authors: C
authors: Botuha
authors: Fabrice
authors: F
authors: Chemla
authors: Alejandro
authors: A
authors: Pérez-Luna
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D007097:Imines / Q000737:chemistry; D008956:Models, Chemical; D009942:Organometallic Compounds / Q000737:chemistry; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry; D015032:Zinc / Q000737:chemistry
chemical_list: D000438:Alcohols; D000475:Alkenes; D000605:Amino Alcohols; D000970:Antineoplastic Agents; D007097:Imines; D009942:Organometallic Compounds; D013452:Sulfonium Compounds; C059688:alkoxyl radical; C522016:sulfinimine; D015032:Zinc; D013110:Sphingosine; C005682:safingol