Chemical transformation of protoberberines. XI A novel synthesis of 2, 3, 10, 11-tetraoxygenated protoberberine alkaloids from corresponding 2, 3, 9, 10- …

M HANAOKA, WONJEA CHO, M MARUTANI…

Index: Hanaoka, Miyoji; Cho, Won Jea; Marutani, Mari; Mukai, Chisato Chemical & Pharmaceutical Bulletin, 1987 , vol. 35, # 1 p. 195 - 199

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Citation Number: 11

Abstract

2, 3, 9, 10-Tetraoxygenated protoberberin alkaloids, berberine (1a), palmatine (1b), and coptisine (1c), were efficiently converted into the corresponding 12-hydroxy-2, 3, 10, 11- tetraoxygenated protoberberines (6a, 6b, 6c) through an oxidative C 8-C 8a bond cleavage with m-chloroperbenzoic acid, followed by the enamide photo-cyclization. On successive treatment with diethyl chlorophosphate and sodium in liquid ammonia, the 12-hydroxy ...