[C:1]([O:9][CH2:10][C:11]1([CH2:16][O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][CH:12]1[CH:14]=C)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:26]=[O+][O-].[BH4-].[Na+]>C(Cl)Cl.C1CCCCC1.C(OCC)(=O)C>[C:18]([O:17][CH2:16][C:11]1([CH2:10][O:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13][CH:12]1[CH2:14][OH:26])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1A solution of 11 g (33 mmoles) of 1,1-bis(benzoyloxymethyl)-2-vinylcyclopropane in 200 ml of CH2Cl2 was cooled to -70° and stirred while a stream of O3 was introduced over a period of 30 minutes, at which time a permanent blue color was obtained. TLC in cyclohexane-ethyl acetate (4:1) indicated that the starting material was no longer present and several new more polar products (Rf 0.55, 0.5, 0.47, 0.4) had been formed. The reaction mixture was treated with 6.6 g (174 mmoles) of NaBH4 and the cooling bath was removed. Stirring was continued for 1.5 hours and TLC showed the formation of a more polar (Rf 0.2) product. The reaction mixture was acidified by the continuous dropwise addition of 200 ml of 2N HCl. The mixture was concentrated to remove the CH2Cl2 and the aqueous layer was extracted with three 100 ml portions of EtOAc which was washed with 50 ml of water, 100 ml of saturated NaHCO3 and 50 ml of saturated NaCl. The EtOAc layer was dried (MgSO4), filtered and concentrated to give 11.3 g of crude product which was chromatographed on 600 ml of silica gel; first eluting with 2400 ml of cyclohexane-ethyl acetate (5:2) and finally with 1600 ml of 2:1 cyclohexane ethyl acetate. Fractions containing only product were combined and concentrated to give 4 g (36%) of the desired compound.
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