A general and concise asymmetric synthesis of sphingosine, safingol and phytosphingosines via tethered aminohydroxylation.
A novel, practical and efficient enantioselective synthesis of sphingoid bases, l-threo-[2S,3S]-sphinganine (safingol), l-threo-[2S,3S]-sphingosine, l-arabino-[2R,3S,4R] and l-xylo-[2R,3S,4S]-C(18)-phytosphingosine is described. The synthetic strategy features the Sharpless kinetic resolution and tethered aminohydroxylation (TA) as the key steps.
Kumar
Pradeep
P
Division of Organic Chemistry, National Chemical Laboratory, Pune 411008, India. pk.tripathi@ncl.res.in
Dubey
Abhishek
A
Puranik
Vedavati G
VG
D000588:Amines / Q000737:chemistry*; D006900:Hydroxylation; D008968:Molecular Conformation; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
D000588:Amines; C012491:phytosphingosine; D013110:Sphingosine; C005682:safingol