O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:15][C:16](=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20].[C:22]1(=O)[CH2:27]CCC=[CH:23]1.F[C:30](F)(F)S(O)(=O)=O.[CH3:37][CH2:38]N(CC)CC>C(Cl)Cl>[CH3:30][C:20]1[CH:15]2[CH2:37][CH2:38][CH:18]([CH2:17][C:16]2=[O:21])[C:19]=1[CH2:23][CH2:22][CH3:27]
Prepared using the method described in Jung, Michael E.; Tetrahedron Letters 2005, 46(30), 5057-5061. To a suspension of 2.8 g of phosphorous pentoxide in 30 mL anh. DCM were added 6.1 mL of 2-hexanone followed by 14.4 mL of 2-cyclohexen-1-one at rt. The suspension was cooled to 0° C. with an ice bath before 13 mL of trifluoromethanesulfonic acid was carefully added. The reaction mixture was warmed to rt and then heated at 40° C. overnight. 27 mL of NEt3 were dropwise added at 0° C., the mixture was stirred at rt for 10 min and then evaporated to dryness. Purification by CC with EtOAc-Hept (25:75) yielded 3.37 g of rac-(1R*,4R*)-6-methyl-5-propyl-bicyclo[2.2.2]oct-5-en-2-one as brown oil.
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