Dimethyl Sulfoxide → 1,4-Dimethyl-7-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulene

Reaction equation

[CH3:1][CH2:2][CH2:3][CH2:4][CH3:5].[CH2:6](O)[CH3:7].[CH:9](O)([CH3:11])[CH3:10].CS(C)=O.[CH2:17](O)C.[CH3:20][CH2:21][CH2:22][CH2:23]CC>>[CH3:10][CH:9]1[CH:11]2[CH2:20][CH2:21][CH:22]([CH3:23])[C:5]2=[CH:4][CH:3]([C:6]([CH3:7])=[CH2:17])[CH2:2][CH2:1]1

Participants

Reactant 5

HCID 679Dimethyl Sulfoxide

HCID 702Ethanol

HCID 8003Pentane2×

HCID 8058Hexane

HCID 22179027Isopropanol ethanol

Product 1

HCID 908051,4-Dimethyl-7-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulene

Procedure

Before experiments as described in this example were started, it was tested which organic solvent could be best used to dissolve the substrate. Stock solutions of 10 mM γ-gurjunene were prepared in hexane, pentane, iso-propanol ethanol and DMSO, and 5 μL of these solutions was added to the incubation-mixture. On the basis of the results of Table III ethanol was chosen as solvent for the substrates in all experiments, instead of the commonly used pentane (e.g. Karp et al., 1990).