Biomimetic formation of macrocyclic spermine alkaloids

Authors
Dimitrov, V Geneste, H Guggisberg, A Hesse, M
Citation
V. Dimitrov et al., Biomimetic formation of macrocyclic spermine alkaloids, HELV CHIM A, 84(7), 2001, pp. 2108-2118
Citations number
29
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
HELVETICA CHIMICA ACTA
ISSN journal
0018019X → ACNP
Volume
84
Issue
7
Year of publication
2001
Pages
2108 - 2118
Database
ISI
SICI code
0018-019X(2001)84:7<2108:BFOMSA>2.0.ZU;2-7
Abstract
Dihydroxyverbacine (10), a precursor for oxidative phenol coupling. was obt ained via (+/-)-buchnerine (14). whose synthesis is described. The oxidizin g system hemin (ferriprotoporphyrin IX chloride)/H2O2 promoted intramolecul ar coupling of 10 to give the alkaloids aphelandrine (1). orantine (2), and chaenorpine (7). The alkaloids were identified by on-line coupled HPLC and atmospheric-pressure chemical-ionization (APCI) mass spectrometry.