ISSN:
0018-019X
Schlagwort(e):
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
Four analogs of the acetylenic alkaloid, histrionicotoxin (C19H25NO) and the allenic alkaloid, isodihydrohistrionicotoxin have been isolated from extracts of skins of the arrow poison frog, Dendrobates histrionicus and characterized as neodihydrohistrionicotoxin, tetrahydrohistrionicotoxin, isotetrahydrohistrionicotoxin and octahydrohistrionicotoxin. These spiropiperidine (8-hydroxy-1-azaspiro[5.5]undecane) alkaloids differ only in the degree of unsaturation in the five carbon atoms (position 2) and four carbon atoms (position 7) side chains. A fifth compound, HTX-D, corresponds in empirical formula to a tetrahydrohistrionicotoxin with a 7-(cis-1-butenyl-3-ynyl) side chain, but the major mass spectral fragmentation with loss of C2H5O is not characteristic of the histrionicotoxins. Reduction of histrionicotoxin with hydrogen and Lindlar catalyst affords an isomeric dihydrohistrionicotoxin with the terminal acetylene of the five carbon atoms side chain reduced, tetrahydrohistrionicotoxin and hexahydrohistrionicotoxins, while reduction with hydrogen and palladium on charcoal affords dodecahydrohistrionicotoxin which is readily methylated to the tertiary amine by methyl iodide.
Zusätzliches Material:
4 Ill.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/hlca.19740570835
Permalink
