Manganese(III) acetate mediated radical reactions leading to araliopsine and related quinoline alkaloids

G  Bar; A F  Parsons; C B  Thomas

Manganese(III) acetate mediated radical reactions leading to araliopsine and related quinoline alkaloids

G Bar, A F Parsons, C B Thomas

Chemistry

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

Abstract

Tricyclic quinoline alkaloids, including araliopsine 2, can be prepared in 'one-pot' by reaction of 4-hydroxy-1-methyl-2(1H)quinoline 5 or 2,4-quinolinediol 31 with manganese(III) acetate in the presence of a variety of electron-rich alkenes. The reaction mechanism involves an initial intermolecular radical addition reaction followed by radical oxidation and cyclisation steps. Both angular and linear tricyclic alkaloids can be formed and the regioselectivity of the cyclisation is shown to depend on whether alkyl or aryl groups are attached to the alkene. (C) 2001 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	4719-4728
Number of pages	10
Journal	Tetrahedron
Volume	57
Issue number	22
Publication status	Published - 28 May 2001

Keywords

alkaloids
manganese and compounds
quinolines
radicals and radical reactions
OLEFINS

Cite this

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title = "Manganese(III) acetate mediated radical reactions leading to araliopsine and related quinoline alkaloids",

abstract = "Tricyclic quinoline alkaloids, including araliopsine 2, can be prepared in 'one-pot' by reaction of 4-hydroxy-1-methyl-2(1H)quinoline 5 or 2,4-quinolinediol 31 with manganese(III) acetate in the presence of a variety of electron-rich alkenes. The reaction mechanism involves an initial intermolecular radical addition reaction followed by radical oxidation and cyclisation steps. Both angular and linear tricyclic alkaloids can be formed and the regioselectivity of the cyclisation is shown to depend on whether alkyl or aryl groups are attached to the alkene. (C) 2001 Elsevier Science Ltd. All rights reserved.",

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author = "G Bar and Parsons, {A F} and Thomas, {C B}",

year = "2001",

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language = "English",

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pages = "4719--4728",

journal = "Tetrahedron",

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T1 - Manganese(III) acetate mediated radical reactions leading to araliopsine and related quinoline alkaloids

AU - Bar, G

AU - Parsons, A F

AU - Thomas, C B

PY - 2001/5/28

Y1 - 2001/5/28

N2 - Tricyclic quinoline alkaloids, including araliopsine 2, can be prepared in 'one-pot' by reaction of 4-hydroxy-1-methyl-2(1H)quinoline 5 or 2,4-quinolinediol 31 with manganese(III) acetate in the presence of a variety of electron-rich alkenes. The reaction mechanism involves an initial intermolecular radical addition reaction followed by radical oxidation and cyclisation steps. Both angular and linear tricyclic alkaloids can be formed and the regioselectivity of the cyclisation is shown to depend on whether alkyl or aryl groups are attached to the alkene. (C) 2001 Elsevier Science Ltd. All rights reserved.

AB - Tricyclic quinoline alkaloids, including araliopsine 2, can be prepared in 'one-pot' by reaction of 4-hydroxy-1-methyl-2(1H)quinoline 5 or 2,4-quinolinediol 31 with manganese(III) acetate in the presence of a variety of electron-rich alkenes. The reaction mechanism involves an initial intermolecular radical addition reaction followed by radical oxidation and cyclisation steps. Both angular and linear tricyclic alkaloids can be formed and the regioselectivity of the cyclisation is shown to depend on whether alkyl or aryl groups are attached to the alkene. (C) 2001 Elsevier Science Ltd. All rights reserved.

KW - alkaloids

KW - manganese and compounds

KW - quinolines

KW - radicals and radical reactions

KW - OLEFINS

M3 - Article

SN - 0040-4020

VL - 57

SP - 4719

EP - 4728

JO - Tetrahedron

JF - Tetrahedron

IS - 22

ER -