ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([O:23][CH3:24])(=[O:22])[CH2:13][C@H:14]([CH2:16][CH2:17][CH:18]=C(C)C)[CH3:15].S([O-])([O-])(=O)=S.[Na+].[Na+].O.O.I(O)(=O)(=O)=O>ClCCl.C1COCC1.O>[CH3:15][C@@H:14]([CH2:16][CH2:17][CH:18]=[O:9])[CH2:13][C:12]([O:23][CH3:24])=[O:22]
To a solution of 7.76 g (36 mmol) of 80% m-chloroperbenzoic acid in 200 ml of dry dichloromethane is added a solution of 6.00 g (32.6 mmol) of (S)-methyl citronellate 30 (prepared in 31-(1)) in 50 ml of dry dichloromethane, and the mixture is stirred at room temperature for one hour. The reaction mixture are added 5% aqueous solution of sodium thiosulfate and a dilute aqueous solution of sodium hydrogencarbonate, and the mixture is extracted with dichloromethane twice. The extract is washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. To a solution of the residue in 80 ml of THF is added a solution of 8.90 g (39 mmol) of periodic acid dihydrate in 80 ml of THF at 0° C. After additional stirring at room temperature for 20 minutes, the reaction mixture is diluted with water, and extracted with ether twice. The extract is washed with water, a saturated aqueous solution of sodium hydrogencarbonate, and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to give 5.2 g of the crude desired aldehyde 31 as an oil, which is employed in the next step without further purification.
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