Issue 12, 1975

Studies of enzyme-mediated reactions. Part V. Synthesis of (13S)- and (13R)-[13-3H1]scoulerine from stereospecifically labelled (R)- and (S)-[α3H1]benzyl alcohols; stereochemistry of enzymic reactions at saturated benzylic carbon

Abstract

A synthesis of (14RS)-scoulerine [as (2)] has been developed which allows stereospecific labelling with deuterium or tritium at C-13; (14RS)-coreximine (45) is a valuable second product from the synthesis. The configurational purity of the labelled scoulerine was determined by degradation of a suitable intermediate, in the 2H series to monodeuteriosuccinic acid, and in the 3H-series to [3H]malic acid for configurational assay by fumarase.

Incorporation experiments with (13R)- and (13S)-[13-3H1]scoulerine have proved that the biosynthesis of both narcotine (6) and chelidonine (7) involves stereospecific removal of the pro-S hydrogen atom from the saturated benzylic carbon, C-13 of scoulerine (2). The mechanistic implications of these findings are considered.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1975, 1162-1171

Studies of enzyme-mediated reactions. Part V. Synthesis of (13S)- and (13R)-[13-3H1]scoulerine from stereospecifically labelled (R)- and (S)-[α3H1]benzyl alcohols; stereochemistry of enzymic reactions at saturated benzylic carbon

A. R. Battersby, J. Staunton, H. R. Wiltshire, B. J. Bircher and C. Fuganti, J. Chem. Soc., Perkin Trans. 1, 1975, 1162 DOI: 10.1039/P19750001162

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