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.