Total synthesis and absolute stereochemistry of pentenocin B, a novel interleukin-1 beta converting enzyme inhibitor

Tsutomu Sugahara; Hayato Fukuda; Yoshiharu Iwabuchi

doi:10.1021/jo035430x

Total synthesis and absolute stereochemistry of pentenocin B, a novel interleukin-1 beta converting enzyme inhibitor

J Org Chem. 2004 Mar 5;69(5):1744-7. doi: 10.1021/jo035430x.

Authors

Tsutomu Sugahara¹, Hayato Fukuda, Yoshiharu Iwabuchi

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan. [email protected]

PMID: 14987040
DOI: 10.1021/jo035430x

Abstract

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.

MeSH terms

Caspase Inhibitors*
Cyclopentanes / chemical synthesis*
Cyclopentanes / chemistry
Cysteine Proteinase Inhibitors / chemical synthesis*
Cysteine Proteinase Inhibitors / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Stereoisomerism

Substances

Caspase Inhibitors
Cyclopentanes
Cysteine Proteinase Inhibitors
pentenocin B