Issue 0, 1973

Quinoline alkaloids. Part XIV. Asymmetric synthesis by the peroxy-acid–olefin reaction. The absolute stereochemistry of balfourodine, isobalfourodine, and related compounds, and the biosynthesis of isomeric dihydrofuro- and dihydropyrano-derivatives

Abstract

Reactions of 3-(3-methylbut-2-enyl)-2,4-dihydroxyquinoline derivatives with (+)- and (–)-peroxycamphoric acid, with (+)- and (–)-peroxyhydratropic acid, and with (+) and (–)-norbornane-2-endo-peroxycarboxylic acid furnished optically active dihydrofuroquinoline alkaloids, balfourodine and O-methylbalfourodinium salt, and the dihydropyranoquinoline, isobalfourodine (2–10% optical induction). The absolute stereochemistry of the alkaloids was determined by ozonolysis to 3-hydroxy-4,4-dimethyl-γ-butyrolactone. The stereochemical results are discussed in relation to the peroxy-acid-olefin reaction, to the balfourodine–isobalfourodine rearrangement, and to the biosynthesis of coumarins and quinolines containing hydroxyisopropyldihydrofuran and hydroxy-dimethyldihydropyran rings.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1973, 626-632

Quinoline alkaloids. Part XIV. Asymmetric synthesis by the peroxy-acid–olefin reaction. The absolute stereochemistry of balfourodine, isobalfourodine, and related compounds, and the biosynthesis of isomeric dihydrofuro- and dihydropyrano-derivatives

R. M. Bowman, J. F. Collins and M. F. Grundon, J. Chem. Soc., Perkin Trans. 1, 1973, 626 DOI: 10.1039/P19730000626

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