Tributylstannane → (13E)-(6RS,9alpha,11alpha,15S)-6,9-Epoxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester

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Reaction Steps

In a Pyrex (registered Trade Mark) vessel, a solution of 540 mg of (13E)-(5RS,6RS,9α,11α,15S)-5-bromo-6,9-epoxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester (prepared as described in Example 1), 322 mg of tri-n-butyl-tinhydride and 24 mg of 2,2'-azobisisobutyronitrile in 6 ml of benzene was irradiated with light from a high pressure mercury lamp at room temperature for 30 minutes. To the reaction mixture was added an aqueous sodium carbonate solution and the mixture was extracted with ethyl acetate. The extract was washed with water and aqueous sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (4:1) as eluent to give 435 mg of the title compound having the following physical characteristics:

Provenance & Evidence