[C:1]([O:5][C@@H:6]1[CH2:10][C@H:9]([O:11]C(=O)C)[CH:8]=[CH:7]1)([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].O.C(Cl)(Cl)Cl>C1COCC1.CO.O>[C:1]([O:5][C@@H:6]1[CH2:10][C@H:9]([OH:11])[CH:8]=[CH:7]1)([CH3:4])([CH3:2])[CH3:3]
Dissolve (-)-acetic acid cis-4-tert-butyloxy-cyclopent-2-enyl ester (90 mg, 0.45 mmol, prepared in example 14) in THF/methanol/water (1.5/0.5/0.5 mL). Add lithium hydroxide monohydrate (23.7 mg) with stirring. After stirring for about 2 hours at room temperature, dilute the reaction with water (10 mL) and extract with tert-butyl methyl ether. Combine the organic phases, dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (silica gel, 2 g, 40% diethyl ether/hexane, 1.5×2.5 cm column) to provide the title compound (71 mg, quantitative yield, 76% ee) as a pale yellow oil, [α]20D =+14.6°, (c 1.03, chloroform).
Wird geladen…
