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Communication | Special issue | Vol 15, No. 2, 1981, pp.709-712
Published online, 1st January, 1970
DOI: 10.3987/S-1981-02-0709
Studies on the Biomimetic Control of the Coupling Position in the Oxidative Ary-Aryl Coupling Reactions of the Bridged Ether Derivatives of O-Methylnorbelladine

Masayuki Murase, Tetsuya Takeya, and Seisho Tobinaga*

*Showa College of Pharmaceutical Sciences, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan

Abstract

Oxidative aryl-aryl coupling reactions of the bridged ether derivatives (10a, 10b) of O-methylnorbelladine were investigated mimicking the enzymatic control of the reaction sites. Oxidation of (10b) by VOF3 gave a para-metha coupling product (12), and (10a) afforded an ortho-metha coupling product (14) and a dimer (15).