Application of the BHQ benzannulation reaction to the synthesis of benzo-fused coumarins

James A. Bull; Cristina Luján; Michael G. Hutchings; Peter Quayle

doi:10.1016/j.tetlet.2009.03.077

Application of the BHQ benzannulation reaction to the synthesis of benzo-fused coumarins

James A. Bull, Cristina Luján, Michael G. Hutchings, Peter Quayle

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Abstract

A new approach to the synthesis of the 6H-benzo[d]naphtha[1,2-b]pyran-6-one ring system present in the gilvocarcin family of antibiotics is described. The key feature of this approach is the application of a new benzannulation strategy (the 'BHQ Reaction') whereby readily available ortho-allylaryl trichloroacetates are transformed into naphthalene derivatives via a cascade of reactions involving an initial ATRC reaction followed by the extrusion of CO2. © 2009 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	3617-3620
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2009.03.077
Publication status	Published - 1 Jul 2009

Keywords

ATRC
Benzannulation
Carbene
Copper
Cyclisation
Kharasch
Lactone
Radical

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10.1016/j.tetlet.2009.03.077

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title = "Application of the BHQ benzannulation reaction to the synthesis of benzo-fused coumarins",

abstract = "A new approach to the synthesis of the 6H-benzo[d]naphtha[1,2-b]pyran-6-one ring system present in the gilvocarcin family of antibiotics is described. The key feature of this approach is the application of a new benzannulation strategy (the 'BHQ Reaction') whereby readily available ortho-allylaryl trichloroacetates are transformed into naphthalene derivatives via a cascade of reactions involving an initial ATRC reaction followed by the extrusion of CO2. {\textcopyright} 2009 Elsevier Ltd. All rights reserved.",

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AU - Bull, James A.

AU - Luján, Cristina

AU - Hutchings, Michael G.

AU - Quayle, Peter

PY - 2009/7/1

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N2 - A new approach to the synthesis of the 6H-benzo[d]naphtha[1,2-b]pyran-6-one ring system present in the gilvocarcin family of antibiotics is described. The key feature of this approach is the application of a new benzannulation strategy (the 'BHQ Reaction') whereby readily available ortho-allylaryl trichloroacetates are transformed into naphthalene derivatives via a cascade of reactions involving an initial ATRC reaction followed by the extrusion of CO2. © 2009 Elsevier Ltd. All rights reserved.

AB - A new approach to the synthesis of the 6H-benzo[d]naphtha[1,2-b]pyran-6-one ring system present in the gilvocarcin family of antibiotics is described. The key feature of this approach is the application of a new benzannulation strategy (the 'BHQ Reaction') whereby readily available ortho-allylaryl trichloroacetates are transformed into naphthalene derivatives via a cascade of reactions involving an initial ATRC reaction followed by the extrusion of CO2. © 2009 Elsevier Ltd. All rights reserved.

KW - ATRC

KW - Benzannulation

KW - Carbene

KW - Copper

KW - Cyclisation

KW - Kharasch

KW - Lactone

KW - Radical

U2 - 10.1016/j.tetlet.2009.03.077

DO - 10.1016/j.tetlet.2009.03.077

M3 - Article

SN - 1873-3581

VL - 50

SP - 3617

EP - 3620

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

Application of the BHQ benzannulation reaction to the synthesis of benzo-fused coumarins

Abstract

Keywords

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