Quinolizidines. XXII. An extension of the" 3-acetylpyridine route" to the syntheses of 9-hydroxy-10-methoxy-and 10-hydroxy-9-methoxybenzo [a] quinolizidine-type …

T FUJII, M OHBA, JUN SAKAGUCHI

Index: Fujii, Tozo; Ohba, Masashi; Sakaguchi, Jun Chemical and Pharmaceutical Bulletin, 1987 , vol. 35, # 9 p. 3628 - 3640

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Citation Number: 12

Abstract

Alternative syntheses of the Alangium alkaloids bearing the 9-hydroxy-10-methoxy-and 10- hydroxy-9-methoxybenzo [a] quinolizidine skeletons (types 3 and 4) have now become feasible through generally applicable routes starting from 3-acetylpyridine. The routes include the mercuric acetate-edetic acid oxidation of the 3-acetylpyridine derivatives 8a, b or the alkaline ferricyanide oxidation of the quaternary salts (29a, b and 30a) of 3- ...