Cis—cis nepetalactol ([4aR,7S,7aS]-4,7-dimethyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-ol) was obtained by reducing 92 mg (0.55 mmol, 1 eq) of cis–cis-nepetalactone with 95 mg of DIBAL (0.66 mmol, 1.2 eq). Under dry conditions and a nitrogen atmosphere, 710 μl of DIBAL dissolved in hexane was added dropwise during 20 min to a dry ice/acetone–cooled flask containing cis—cis nepetalactone in 5 ml of hexane while stirring. After stirring for another hour, 770 mg of Bäckstrøm reagent (sodium sulfate decahydrate:celite, 1:1, v/v) was added, and the reaction was stirred for another hour on ice. Solid particles were removed by filtration on a glass frit, which was washed with diethyl ether. The residue obtained after removal of solvent under reduced pressure was purified by silica flash chromatography (1.5 × 21 cm column, eluted with up to 20% ethyl acetate in hexane), yielding 35 mg of product (0.21 mmol, 38% yield) as a 70:30 mix of C1 anomers according to NMR. 1H NMR (major anomer): δ 6.02 (1H, dq, J = 1.4/1.4 Hz, C3), 5.01 (1H, dd, J = 6.2/5.4 Hz, C1), 2.72 (1H, d, J = 6.3 Hz, O1), 2.47 (1H, broad ddd, J = 7/7/7 Hz, C4a), 2.26–2.20 (1H, m, C7), 2.16–2.08 (1H, m, C7a), 1.87–1.79 (1H, m, C5), 1.82–1.72 (1H, m, C6), 1.59–1.51 (1H, m, C5), 1.55 (3H, dd, J = 1.1/1.4 Hz, C8), 1.35–1.25 (1H, m, C6), 1.09 (3H, d, J = 7.1 Hz, C9); 13C NMR (major anomer): δ 134.58 (C3), 113.81 (C4), 92.85 (C1), 45.53 (C7a), 38.51 (C4a), 36.01 (C7), 32.54 (C6), 29.70 (C5), 16.73 (C9), 16.47 (C8); 1H NMR (minor anomer): δ 5.98 (1H, dq, J = 1.5/1.5 Hz, C3), 5.33 (1H, dd, J = 5.0/3.3 Hz, C1), 2.52 (1H, dd, J = 5.0/1.3 Hz, O1), 2.38–2.20 (1H, m, C7), 2.36–2.29 (1H, m, C4a), 2.20–2.12 (1H, m, C7a), 2.19–2.10 (1H, m, C5), 1.64–1.53 (1H, m, C5), 1.60 (3H, dd, J = 0.9/1.4 Hz, C8), 1.15 (3H, d, J = 7.0, C9), C6 is not assigned; 13C NMR (minor anomer): δ 132.55 (C3), 92.75 (C1), 44.46 (C7a), 38.99 (C4a), 36.71 (C7), 30.97 (C5), 17.24 (C8), 15.29 (C9), C4 and C6 are not assigned.