Haemultine and the Alkaloids of Haemanthus multiflorus Martyn1

The Journal of Organic Chemistry
1961.0

Abstract

An investigation of the alkaloids of Haemanthus multiflorus Martyn has shown the presence of lycorine and montanine. No haemultine, previously reported by other workers to occur in this source, could be detected. Demethoxylation of either crinamine or haemanthamine with sodium and amyl alcohol affords two isomeric demethoxy derivatives (II and III) as well as the respective dihydro compounds. Addition of methylmagnesium iodide to 2,5-dimethyl-9-oxo-6,7-benzomorphan methobromide (II) has afforded the 9-methylcarbinol methiodide (III) with the hydroxyl oriented toward the cis-fused iminoethano system as shown by degradation to the known cis-fused furan derivatives IV and VIII. Pyrolysis of III in boiling 1-nonanol yielded the base VII. Methyllithium and the free base VI on the other hand produced the diastereoisomer (X) which was also degraded to a nitrogen-free compound, presumably the trans-fused furan XI. A similar stereochemical pattern was followed in the addition of hydrogen to II and VI. Spectral data furnished additional proof of our assignments which are in conformity with and confirmatory of those made in the 2'-methoxy series (cf. References 1 and 2). Compounds VII, X, XIII, XV, and the O-acetyl derivative of XV have been tested for analgesic activity.

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