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; Ninoska Flores; María A. Bucio; Nury Pérez-Hernández; Pedro Joseph-Nathan

doi:10.1021/ol900065x

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, Ninoska Flores, María A. Bucio, Nury Pérez-Hernández, Pedro Joseph-Nathan

Research output: Contribution to journal › Article › peer-review

49 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 language	English
Pages (from-to)	1491-1494
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	7
DOIs	https://doi.org/10.1021/ol900065x
State	Published - 2 Apr 2009
Externally published	Yes

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10.1021/ol900065x

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

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.",

author = "Cedr{\'o}n, {Juan C.} and Ana Est{\'e}vez-Braun and Ravelo, {{\'A}ngel G.} and David Guti{\'e}rrez and Ninoska Flores and Bucio, {Mar{\'i}a A.} and Nury P{\'e}rez-Hern{\'a}ndez and Pedro Joseph-Nathan",

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doi = "10.1021/ol900065x",

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T1 - Bioactive montanine derivatives from halide-induced rearrangements of haemanthamine-type alkaloids. Absolute configuration by VCD

AU - Cedrón, Juan C.

AU - Estévez-Braun, Ana

AU - Ravelo, Ángel G.

AU - Gutiérrez, David

AU - Flores, Ninoska

AU - Bucio, María A.

AU - Pérez-Hernández, Nury

AU - Joseph-Nathan, Pedro

PY - 2009/4/2

Y1 - 2009/4/2

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=64349106550&partnerID=8YFLogxK

U2 - 10.1021/ol900065x

DO - 10.1021/ol900065x

M3 - Artículo

SN - 1523-7060

VL - 11

SP - 1491

EP - 1494

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

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

Abstract

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