Image from Google Jackets

251. Die Struktur des Spermin-Alkaloides Aphelandrin aus Aphelandra squarrosa NEES 170. Mitteilung uber organische Naturstoffe

Tipo de material: TextoTextoSeries ; Helvetica Chimica Acta, 61(7), p.2646-2671, 1978Trabajos contenidos:
  • Von Peter Datwyler
  • Bosshardt, H
  • Bernhard, H.O
  • Und Manfred Hesse
  • Und Siegfried Johne
Recursos en línea: Resumen: The new spermine alkaloid aphelandrine (2)has been isolated from Aphelandra squarrosa NEES. By oxidation of 2 with KMn04 followed by methylation (CH2N2)12 and 14 could be prepared (Scheme 2). Fusion of 2 with KOH yielded spermine (1)whereas hydrolysis of 2 in hot hydrochloric acid results in lacton 17, the structure of which could be elucidated by comparison with a synthetically prepared model compound (Scheme 3). The benzylic bonds N (lo), C (1 1)as well as 0 (16), C (17)of 2 could be cleaved by hydrogenolysis (compare 23 and 26; Scheme 4). The elucidation of the correct linkage of the spermine moiety with the aromatic dicarboxylic acid is based mainly on chemical and spectroscopic evidence of the tetrahydro derivative 26, the Hofmann-degradation products 28,30 and 31 (Scheme 6)as well as the ester 35, prepared by partial hydrolysis of 2 (Scheme 7).
Tags from this library: No tags from this library for this title. Log in to add tags.
Star ratings
    Average rating: 0.0 (0 votes)
Holdings
Item type Current library Collection Call number Status Date due Barcode
Documentos solicitados Documentos solicitados CICY Documento préstamo interbibliotecario Ref1 B-12639 (Browse shelf(Opens below)) Available

The new spermine alkaloid aphelandrine (2)has been isolated from Aphelandra squarrosa NEES. By oxidation of 2 with KMn04 followed by methylation (CH2N2)12 and 14 could be prepared (Scheme 2). Fusion of 2 with KOH yielded spermine (1)whereas hydrolysis of 2 in hot hydrochloric acid results in lacton 17, the structure of which could be elucidated by comparison with a synthetically prepared model compound (Scheme 3). The benzylic bonds N (lo), C (1 1)as well as 0 (16), C (17)of 2 could be cleaved by hydrogenolysis (compare 23 and 26; Scheme 4). The elucidation of the correct linkage of the spermine moiety with the aromatic dicarboxylic acid is based mainly on chemical and spectroscopic evidence of the tetrahydro derivative 26, the Hofmann-degradation products 28,30 and 31 (Scheme 6)as well as the ester 35, prepared by partial hydrolysis of 2 (Scheme 7).

There are no comments on this title.

to post a comment.