Total synthesis and absolute stereochemistry of pentenocin B, a novel interleukin-1 beta converting enzyme inhibitor.
Four possible diastereomers of pentenocin B were synthesized in a stereocontrolled manner, and the first total synthesis of a natural enantiomer of (+)-pentenocin B unequivocally established the absolute stereochemistry to be 4S,5R,6R.
Sugahara
Tsutomu
T
Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan. iwabuchi@mail.pharm.tohoku.ac.jp
Fukuda
Hayato
H
Iwabuchi
Yoshiharu
Y
D061945:Caspase Inhibitors; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D015853:Cysteine Proteinase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D061945:Caspase Inhibitors; D003517:Cyclopentanes; D015853:Cysteine Proteinase Inhibitors; C401264:pentenocin B