Expedient synthesis of ialibinones A and B by manganese(III)-mediated oxidative free radical cyclisation

Nigel Simpkins; Michael Weller

doi:10.1016/j.tetlet.2010.07.025

Expedient synthesis of ialibinones A and B by manganese(III)-mediated oxidative free radical cyclisation

Nigel Simpkins, Michael Weller

Chemistry

Research output: Contribution to journal › Article

20 Citations (Scopus)

Abstract

The tricyclic natural products ialibinone A and ialibinone B were prepared as a 41:59 mixture in four steps starting from phloroglucinol. The synthetic sequence involved (i) acylation of phloroglucinol under Friedel-Crafts conditions, (ii) double prenylation using phase-transfer methodology, (iii) dearomatising methylation, and (iv) oxidative free radical cyclisation using manganese(III) acetate. (C) 2010 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	4823-4826
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2010.07.025
Publication status	Published - 1 Sept 2010

Keywords

Total synthesis
Free radical cyclisation
Dearomatisation
Electron-rich aromatics
Acylphloroglucinol

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10.1016/j.tetlet.2010.07.025

Rapid synthesis of complex bioactive alkaloids
Simpkins, N.
Engineering & Physical Science Research Council
1/10/09 → 30/09/12
Project: Research Councils

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title = "Expedient synthesis of ialibinones A and B by manganese(III)-mediated oxidative free radical cyclisation",

abstract = "The tricyclic natural products ialibinone A and ialibinone B were prepared as a 41:59 mixture in four steps starting from phloroglucinol. The synthetic sequence involved (i) acylation of phloroglucinol under Friedel-Crafts conditions, (ii) double prenylation using phase-transfer methodology, (iii) dearomatising methylation, and (iv) oxidative free radical cyclisation using manganese(III) acetate. (C) 2010 Elsevier Ltd. All rights reserved.",

keywords = "Total synthesis, Free radical cyclisation, Dearomatisation, Electron-rich aromatics, Acylphloroglucinol",

author = "Nigel Simpkins and Michael Weller",

year = "2010",

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doi = "10.1016/j.tetlet.2010.07.025",

language = "English",

volume = "51",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Expedient synthesis of ialibinones A and B by manganese(III)-mediated oxidative free radical cyclisation

AU - Simpkins, Nigel

AU - Weller, Michael

PY - 2010/9/1

Y1 - 2010/9/1

N2 - The tricyclic natural products ialibinone A and ialibinone B were prepared as a 41:59 mixture in four steps starting from phloroglucinol. The synthetic sequence involved (i) acylation of phloroglucinol under Friedel-Crafts conditions, (ii) double prenylation using phase-transfer methodology, (iii) dearomatising methylation, and (iv) oxidative free radical cyclisation using manganese(III) acetate. (C) 2010 Elsevier Ltd. All rights reserved.

AB - The tricyclic natural products ialibinone A and ialibinone B were prepared as a 41:59 mixture in four steps starting from phloroglucinol. The synthetic sequence involved (i) acylation of phloroglucinol under Friedel-Crafts conditions, (ii) double prenylation using phase-transfer methodology, (iii) dearomatising methylation, and (iv) oxidative free radical cyclisation using manganese(III) acetate. (C) 2010 Elsevier Ltd. All rights reserved.

KW - Total synthesis

KW - Free radical cyclisation

KW - Dearomatisation

KW - Electron-rich aromatics

KW - Acylphloroglucinol

U2 - 10.1016/j.tetlet.2010.07.025

DO - 10.1016/j.tetlet.2010.07.025

M3 - Article

VL - 51

SP - 4823

EP - 4826

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

Expedient synthesis of ialibinones A and B by manganese(III)-mediated oxidative free radical cyclisation

Abstract

Keywords

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Projects

Rapid synthesis of complex bioactive alkaloids

Cite this