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Issue 0, 1980
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Lythraceous alkaloids. Part 11. Total synthesis of (±)-lythranidine

Abstract

The total synthesis of (±)-lythranidine (1), a cyclophane alkaloid from Lythrum anceps Makino, has been achieved through a sequence of reactions including the following key steps : the Wittig reaction of an ylide (6) with a dialdehyde (3), epimerisation of a cis-2,6-disubstituted piperidine into the desired trans-isomer through the N-nitroso-derivative (11), amidoacetalisation of a mixture of stereoisomeric diols (12) to isolate the desired compound (13), and its partial demethylation followed by hydrolysis.

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Article type: Paper
DOI: 10.1039/P19800001066
Citation: J. Chem. Soc., Perkin Trans. 1, 1980,0, 1066-1069
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    Lythraceous alkaloids. Part 11. Total synthesis of (±)-lythranidine

    K. Fuji, K. Ichikawa and E. Fujita, J. Chem. Soc., Perkin Trans. 1, 1980, 0, 1066
    DOI: 10.1039/P19800001066

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