Bioactive montanine derivatives from halide-induced rearrangements of haemanthamine-type alkaloids. Absolute configuration by VCD

Juan C. Cedrón, Ana Estévez-Braun, Ángel G. Ravelo, David Gutiérrez, Esther Ninoska Flores Quisbert Flores Quisbert, María A. Bucio, Nury Pérez-Hernández, Pedro Joseph-Nathan

Research output: Contribution to journalArticlepeer-review

42 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)1491-1494
Number of pages4
JournalOrganic Letters
Volume11
Issue number7
DOIs
StatePublished - 2 Apr 2009

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