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Review | Regular issue | Vol 1, No. 1, 1973, pp.73-128
Published online, 1st January, 1970
DOI: 10.3987/R-1973-01-0073
Partial Ether Cleavage of Methoxy and Methylenedioxy-substituted Isoquinoline Alkaloids

Sidney Teitel* and Arnold Brossi

*The Department of Chemistry Research, Hoffman-La Roche Inc., Nutley, New Jersey 07110, U.S.A.

Abstract

A variety of polymethoxy-substituted isoquinolines have been preferentially O-demethylated with mineral acid and the procedure applied to the facile synthesis of the alkaloids corypalline (46), cherylline (48), multifloramine (51), anhalonine (2) and lophophorine (54). The method of selective O-demethylenation of methylenedioxy-dimethoxy-substituted isoquinolines with boron trichloride was utilized for the conversion of the phthalide alkaloid (-)-β-hydrastine (6) into (-)-cordrastine II (7).