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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
Author(s) -
Kametani T.,
Agui H.,
Saito K.,
Fukumoto K.
Publication year - 1969
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570060402
Subject(s) - chemistry , mass spectrum , platinum , stereochemistry , product (mathematics) , organic chemistry , medicinal chemistry , catalysis , ion , geometry , mathematics
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 C 5 ‐ and C 6 ‐positions.