Stereocontrolled synthesis of a sphingomyelin methylene analogue as a sphingomyelinase inhibitor.
[reaction: see text]Efficient synthesis of a sphingomyelin methylene analogue, which was designed as a sphingomyelinase inhibitor, was stereoselectively achieved. The Hofmann rearrangement of the alpha-hydroxyethyl-beta-hydroxy amide 4 followed by the intramolecular oxazolidinone ring formation was one of the key steps.
Hakogi
T
T
School of Science, Kwansei Gakuin University, Uegahara, Nishinomiya, Japan.
Monden
Y
Y
Iwama
S
S
Katsumura
S
S
D001409:Bacillus cereus / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D013108:Sphingomyelin Phosphodiesterase / Q000037:antagonists & inhibitors* / Q000737:chemistry; D013109:Sphingomyelins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D013109:Sphingomyelins; D013108:Sphingomyelin Phosphodiesterase