High-yielding synthesis of sphingoid-type bases.
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%).
Séguin
Catherine
C
UPMC-Univ Paris 06, CNRS UMR 7201, Institut Parisien de Chimie Moléculaire (FR 2769), case 183, 4 place Jussieu, F-75005 Paris, France.
Ferreira
Franck
F
Botuha
Candice
C
Chemla
Fabrice
F
Pérez-Luna
Alejandro
A
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
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