Structure and absolute configuration of nyasol and hinokiresinol via synthesis and vibrational circular dichroism spectroscopy.
The absolute configuration of the norlignan (+)-nyasol was determined to be S by comparison of the experimental vibrational circular dichroism data with first-principle calculations taking into account the eight lowest energy conformations. The established absolute configuration of (+)-nyasol enables establishment of the absolute configuration of (-)-hinokiresinol, which is concluded to be S. A total synthesis and resolution of hinokiresinol has been performed to resolve the conflicting reports of the coupling constant of the vinylic protons of the disubstituted double bond in this molecule. Racemic hinokiresinol was resolved. Both enantiomers possess the same antiplasmodial activity.
Lassen
Peter R
PR
The Quantum Protein Centre, Department of Physics, Technical University of Denmark, DK 2800 Lyngby, Denmark.
Skytte
Dorthe Mondrup
DM
Hemmingsen
Lars
L
Nielsen
Simon Feldbaek
SF
Freedman
Teresa B
TB
Nafie
Laurence A
LA
Christensen
S Brøgger
SB
D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002942:Circular Dichroism; D017705:Lignans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D010963:Plasmodium falciparum / Q000187:drug effects*; D013237:Stereoisomerism
D000962:Antimalarials; D017705:Lignans; D010636:Phenols; C119821:hinokiresinol; C109393:nyasol