Water → 3,3a,4,5,6,6a-hexahydro-2H-pentalen-1-one

Participants

Reaction Steps

A stirred solution of 6-[(E)-3-cyclohexyl-(mixture of 3α and 3β)-hydroxyprop-1-enyl]-3-[(E)-4-methoxycarbonylbutylidene]bicyclo[3,3,0]octan-2-one (20 mg), prepared as described in Example 8 and predominantly in the 6β-configuration, otherwise known as (±)-methyl(5E,13E)-(9S),[mixture of (15R) and (15S)]-6a-oxo-6,9-methano-15-cyclohexyl-15-hydroxy-16,17,18,19,20-pentanorprosta-5,13-dienoate, in methanol (3.2 ml) was treated with lithium hydroxide (33.8 mg) and water (1.1 ml) at 20° C. and stirred for 2 hours. The mixture was then concentrated in vacuo. The resulting residue was diluted with water (5 ml) and then acidified to pH 3 by treatment with dilute hydrochloric acid (2N). The aqueous layer was then extracted with ethyl acetate (5×5 ml). The combined organic extracts were dried over anhydrous sodium sulphate and concentrated in vacuo. The resulting residue was subjected to chromatography on a silica gel column, using a mixture of ethyl acetate, hexane and formic acid (50:50:1 by volume) as eluant, to give 3-[(E)-4-carboxybutylidene]-6-[(E)-3-cyclohexyl-(mixture of 3α and 3β)-hydroxyprop-1-enyl]bicyclo[3,3,0]octan-2-one (10 mg), predominantly in the 6β-configuration, otherwise known as (±)-(5E,13E)-(9S),[mixture of (15R) and (15S)]-6a-oxo-6,9-methano-15-cyclohexyl-15-hydroxy-16,17,18,19,20-pentanorprosta-5,13-dienoic acid [NMR in deuterochloroform: multiplets at 6.5, 5.5, 4.2-3.5, 3.0-0.7 p.p.m⟧

Provenance & Evidence