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N ( a ) ‐Demethylseredamin, ein neues Alkaloid aus Rauwolfia sumatrana ; absolute Konfiguration von Seredamin. 140. Mitteilung über Alkaloide
Author(s) -
Hanaoka M.,
Hesse M.,
Schmid H.
Publication year - 1970
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19700530721
Subject(s) - chemistry , apocynaceae , ajmaline , stereochemistry , alkaloid , derivative (finance) , indole test , indole alkaloid , absolute configuration , traditional medicine , medicine , economics , financial economics , cardiology
From Rauwolfia sumatrana Jack (Apocynaceae) the two new indole alkaloids serpentinine and N ( a ) ‐demethylseredamine were isolated. By chemical and spectroscopic evidence and by correlation experiments the latter was shown to have structure 2 . the exact position of the aromatic methoxyl group was established by an investigation of the brominated derivative 12 . The aromatic ORD. Cotton effect of N ( a ) ‐acetyl‐N ( a ) ‐demethyl‐seredamine ( 5 ) and its O‐acetyl derivative 4 as well as the ketone Cotton effect of purpeline ( 9 ) suggest that all the alkaloids of the seredamine group have the same absolute stereochemistry as ajmaline ( 1 ). This was confirmed by a direct chemical correlation of seredamine ( 7 ) with ajmaline.