Straightforward synthesis of sphinganines via a serine-derived Weinreb amide.
Sphinganines can be synthesized in just three steps from easily prepared serine-derived Weinreb amide 4. Pre-deprotonation of the acidic (N-H and O-H) protons of 4 allows for its efficient conversion to amino ketones 5. Such ketones can be selectively reduced to either erythro- or threo-sphinganines. Partially protected sphinganines 11 are also readily accessible in five steps from 4. Thus, Weinreb amide 4 represents one of the most versatile templates described to date for sphinganine synthesis.
So
Regina C
RC
Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, USA.
Ndonye
Rachel
R
Izmirian
Douglas P
DP
Richardson
Stewart K
SK
Guerrera
Robyn L
RL
Howell
Amy R
AR
D000577:Amides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D012694:Serine / Q000737:chemistry*; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000577:Amides; D007659:Ketones; D009942:Organometallic Compounds; D012694:Serine; D013110:Sphingosine; C005682:safingol