10.1021/np049647d.s008 Ilme Liblikas Ilme Liblikas Ellen M. Santangelo Ellen M. Santangelo Johan Sandell Johan Sandell Peter Baeckström Peter Baeckström Mats Svensson Mats Svensson Ulla Jacobsson Ulla Jacobsson C. Rikard Unelius C. Rikard Unelius Simplified Isolation Procedure and Interconversion of the Diastereomers of Nepetalactone and Nepetalactol American Chemical Society 2005 epimerization procedure quantum chemical density Simplified Isolation Procedure method 7 S Nepeta racemosa nepetalactone diastereomer faass énii NMR nepetalactol 2005-06-24 00:00:00 Dataset https://acs.figshare.com/articles/dataset/Simplified_Isolation_Procedure_and_Interconversion_of_the_Diastereomers_of_Nepetalactone_and_Nepetalactol/3280699 Three nepetalactones were isolated from <i>Nepeta racemosa (mussinii</i>) by traditional methods. An improved method was developed to isolate nepetalactones from<i> N. faassénii</i>. An epimerization procedure was used to prepare the fourth 7<i>S-</i>nepetalactone diastereomer. The <i>cis-</i>fused nepetalactols were prepared by reduction of the corresponding nepetalactones, while the <i>trans-</i>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.