Bioactive montanine derivatives from halide-induced rearrangements of haemanthamine-type alkaloids. Absolute configuration by VCD.
An unexpected rearrangement of haemanthamine-type alkaloids in the presence of halogenating agents has been found. Rearranged compounds present the 5,11-methanomorphantridine framework characteristic of montanine-type alkaloids. These compounds are difficult to obtain because of their scarcity in natural sources and because the synthetic approaches developed so far require numerous steps. Vibrational circular dichroism (VCD) spectroscopy was used to determine the absolute configuration of one of the rearranged compounds. Several rearranged alkaloids showed antimalarial activity.
Cedrón
Juan C
JC
Instituto Universitario de Bio-Organica "Antonio Gonzalez", Universidad de La Laguna, Av. Astrofísico Francisco Sanchez 2, 38206 La Laguna-Tenerife, Spain.
Estévez-Braun
Ana
A
Ravelo
Angel G
AG
Gutiérrez
David
D
Flores
Ninoska
N
Bucio
María A
MA
Pérez-Hernández
Nury
N
Joseph-Nathan
Pedro
P