Dihydroxylation of 2-vinylaziridine: efficient synthesis of D-ribo-phytosphingosine.
An efficient and highly stereoselective synthesis of D-ribo-(2S,3S,4R)-phytosphingosine was accomplished in 62% overall yield starting from commercially available (2S)-hydroxymethylaziridine via osmium-catalyzed asymmetric dihydroxylation as a key step.
Yoon
Hyo Jae
HJ
Department of Chemistry and Program of Integrated Biotechnology, Sogang University, Seoul, 121-742, Korea.
Kim
Yong-Woo
YW
Lee
Baeck Kyoung
BK
Lee
Won Koo
WK
Kim
Yongeun
Y
Ha
Hyun-Joon
HJ
D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D006900:Hydroxylation; D008968:Molecular Conformation; D015394:Molecular Structure; D009992:Osmium / Q000737:chemistry; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D001388:Aziridines; D009992:Osmium; C012491:phytosphingosine; D013110:Sphingosine