Simplified isolation procedure and interconversion of the diastereomers of nepetalactone and nepetalactol.
Three nepetalactones were isolated from Nepeta racemosa (mussinii) by traditional methods. An improved method was developed to isolate nepetalactones from N. faassénii. An epimerization procedure was used to prepare the fourth 7S-nepetalactone diastereomer. The cis-fused nepetalactols were prepared by reduction of the corresponding nepetalactones, while the trans-fused nepetalactols were unstable and found to undergo ring-opening reactions yielding iridodials. The characterizations and structural assignments by means of NMR agree with quantum chemical density functional calculations.
Liblikas
Ilme
I
Laboratory of Ecochemistry, Estonian Agricultural University, Tartu.
Santangelo
Ellen M
EM
Sandell
Johan
J
Baeckström
Peter
P
Svensson
Mats
M
Jacobsson
Ulla
U
Unelius
C Rikard
CR
D000818:Animals; D001042:Aphids / Q000502:physiology; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000081004:Cyclopentane Monoterpenes; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D008958:Models, Molecular; D015394:Molecular Structure; D027521:Nepeta / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D012724:Sex Attractants / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D000081004:Cyclopentane Monoterpenes; D003517:Cyclopentanes; D011753:Pyrones; D012724:Sex Attractants; C497341:nepetalactol; C115644:nepetalactone