The terminal olefin, O-methylptelefolonium iodide (5; X = I), was synthesised from the hydroxyisopropyldihydrofuroquinoline (4) by successive dehydration and methylation. Dehydration of the tertiary alcohol (9a) with triphenyl phosphite dibromide and then hydroxylation furnished (±)-dubinidine (8).
J. L. Gaston, M. F. Grundon and K. J. James, J. Chem. Soc., Perkin Trans. 1, 1980, 1136 DOI: 10.1039/P19800001136
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