Direct Conversion of S-(+)-Bulbocapnine into S-(+)-2-Hydroxy-10-methoxyaporphine |
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| Authors: | Kenner C Rice Arnold Brossi |
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| Institution: | Laboratory of Chemistry , National Institute of Arthritis, Metabolism and Digestive Diseases , Bethesda, Maryland, 20014 |
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| Abstract: | The opening of a methylenedioxy group with simultaneous elimination of an oxygen atom during sodium in liquid ammonia reduction is a well established process in the aporphine alkaloid series1. It has furthermore been reported that phosphate esters of phenols are deoxygenated under similar reaction conditions2. The alkaloid bulbocapnine (1) contains an aromatic methylendioxy group and a phenolic hydroxy group; it thus seemed indicated to attempt the direct removal of two oxygen atoms by treating the phosphate ester 2 with an alkali metal in liquid ammonia. We now would like to give experimental details regarding this practical step which was summarized elsewhere3. |
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