Studies on the syntheses of heterocyclic compounds. Part CCCXV erythrinan and related compounds. II . An alternative synthesis of cis-16-hydroxy-15-methoxyerythrinan-8-one and its mass spectrum†‡

Phenolic cyclization of 2-ethoxycarbonylmethylidenecyclohexanone (IV) with 3-hydroxy-4-methoxyphenethylamine (V) were performed in the process of finding a synthetic approach to dihydroerysolidine (I). Thus, 16-hydroxy-15-methoxyerythrinan-6-ene-8-one (VI) and 16-hydroxy-15-methoxyerythrinan-7-ene-8-one (VII) were synthesized, both of which were hydrogenated in the presence of Adams platinum to give the same product (XI). Furthermore, on the basis of the mass spectra of XI and XII, these compounds were assumed to be stereoisomeric at the C5- and C6-positions.

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