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Issue 5, 1991
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Stereoselective and regioselective functionalisation of protopine alkaloids: the synthesis of 1-substituted O-methyldihydrocryptopines

Abstract

Regio- and diastereo-selective complexation of dihydrocryptopine to the tricarbonylchromium(0) unit proceeds in good yield to give a single diastereoisomer with the chromium attached to the dimethoxyarene ring. An X-ray crystal structure analysis on the product revealed an exo disposition of the metal unit relative to the 14-hydroxy group, O-Methylation gave exo-tricarbonyl(η6-O-methyldihydrocryptopine)chromium(0) which was also the exclusive product of the direct complexation of O-methyldihydrocryptopine. Subsequent deprotonation, alkylation (MeI, CH2N+Me2I) and decomplexation gave the corresponding 1-substituted O-methyldihydrocryptopines.

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Article type: Paper
DOI: 10.1039/P19910001019
Citation: J. Chem. Soc., Perkin Trans. 1, 1991,0, 1019-1025
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    Stereoselective and regioselective functionalisation of protopine alkaloids: the synthesis of 1-substituted O-methyldihydrocryptopines

    S. G. Davies, C. L. Goodfellow, J. M. Peach and A. Waller, J. Chem. Soc., Perkin Trans. 1, 1991, 0, 1019
    DOI: 10.1039/P19910001019

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