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Stereochemistry of the Tropane Alkaloids

Abstract

THE respective C3-configurations of the epimeric N-acyl-nortropins have been recently established from the different behaviour of the epimers1 in acyl migration, N → O. Naturally occurring psi-tropine derivatives seem on this basis to contain a hydroxyl group syn-placed to the ring-nitrogen. Atropine, hyoscyamine, convolamine, being hydrolysable to tropine or nortropine, appear, therefore, to represent anti-3-tropanol structures.

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FODOR, G. Stereochemistry of the Tropane Alkaloids. Nature 170, 278–279 (1952). https://doi.org/10.1038/170278a0

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