1. Constituents of Rhizoma nupharis. XXII. Structure of Nuphamine
- Author
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Yoshio Arata and Tsutomu Ohashi
- Subjects
Steric effects ,Magnetic Resonance Spectroscopy ,Chemical Phenomena ,biology ,Chemistry ,Stereochemistry ,Alkaloid ,Nupharamine ,Selective catalytic reduction ,General Chemistry ,General Medicine ,biology.organism_classification ,Medicinal chemistry ,chemistry.chemical_compound ,Alkaloids ,Thionyl chloride ,Drug Discovery ,Nuphar - Abstract
A new alkaloid (I), C15H23O2N has been isolated from Nuphar japonicum DC. and named nuphamine. The compound (III) obtained by the catalytic reduction after the chlorination of I with thionyl chloride is completely in accordance with (-)-desoxynupharamine, derived from nupharamine (IX). By the catalytic reduction of I with palladium-carbon, dihydronuphamine (V), (-)-deoxynupharidine (VI-A) and allodeoxynupharidine (VI-B) were prepared. VI-A and VI-B were also prepared from V. Judging from these reactions and the nuclear magnetic resonance spectra, the structure of I has been determined to be presented by the fromula VIII. The steric chemical correlations among the alkaloids, (-)-desoxynupharidine (VI-A), (-)-nuphamine (VIII) and (-)-nupharamine (IX) isolated from Nuphar iaponicum have been also achieved.
- Published
- 1965
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