The Journal of Organic Chemistry

Addition of dichlorocarbene to oxyberberine and berberine

G Manikumar, M Shamma

Index: Manikumar, Govindarajan; Shamma, Maurice Journal of Organic Chemistry, 1981 , vol. 46, # 2 p. 386 - 389

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Citation Number: 16

Abstract

Dichlorocarbene adds to oxyberberine (2) to furnish the key adduct 5. Hydrolysis of 5 in dilute hydrochloric acid yields oxyberberine-13-carboxaldehyde (7). Reduction of adduct 5 with zinc in acetic acid produces 13-methyloxyberberine (1 1). Alternatively, reduction of 5 with lithium aluminum hydride in hot THF leads to enlargement of ring C with formation of the vinylic chloride 14. A complex transformation occurs when 5 is refluxed in aqueous ...