A double oxidation procedure for the preparation of halogen-substituted para-benzoquinone monoketals: asymmetric synthesis of (-)-harveynone

Daniel R. Hookins; Richard J. K. Taylor

doi:10.1016/j.tetlet.2010.10.047

A double oxidation procedure for the preparation of halogen-substituted para-benzoquinone monoketals: asymmetric synthesis of (-)-harveynone

Daniel R. Hookins, Richard J. K. Taylor

Chemistry

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

Abstract

The double oxidation of halophenols with hypervalent iodine reagents in methanol provides a simple procedure to prepare halo-1,4-benzoquinone monoketals. Seven examples of this procedure are reported as is the conversion of 3-iodo-4,4-dimethoxycyclohexa-2,5-dienone into the natural product, (-)-harveynone. (C) 2010 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	6619-6621
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2010.10.047
Publication status	Published - 15 Dec 2010

Keywords

ANODIC-OXIDATION
ABSOLUTE-CONFIGURATION
EFFICIENT
CYCLOHEXA-2,5-DIENONES
(+)-PANEPOPHENANTHRIN
(-)-TRICHOLOMENYN
(+)-EPIEPOFORMIN
(+)-OTTELIONE-A
ASSIGNMENT
PHENOLS

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10.1016/j.tetlet.2010.10.047

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title = "A double oxidation procedure for the preparation of halogen-substituted para-benzoquinone monoketals: asymmetric synthesis of (-)-harveynone",

abstract = "The double oxidation of halophenols with hypervalent iodine reagents in methanol provides a simple procedure to prepare halo-1,4-benzoquinone monoketals. Seven examples of this procedure are reported as is the conversion of 3-iodo-4,4-dimethoxycyclohexa-2,5-dienone into the natural product, (-)-harveynone. (C) 2010 Elsevier Ltd. All rights reserved.",

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T1 - A double oxidation procedure for the preparation of halogen-substituted para-benzoquinone monoketals: asymmetric synthesis of (-)-harveynone

AU - Hookins, Daniel R.

AU - Taylor, Richard J. K.

PY - 2010/12/15

Y1 - 2010/12/15

N2 - The double oxidation of halophenols with hypervalent iodine reagents in methanol provides a simple procedure to prepare halo-1,4-benzoquinone monoketals. Seven examples of this procedure are reported as is the conversion of 3-iodo-4,4-dimethoxycyclohexa-2,5-dienone into the natural product, (-)-harveynone. (C) 2010 Elsevier Ltd. All rights reserved.

AB - The double oxidation of halophenols with hypervalent iodine reagents in methanol provides a simple procedure to prepare halo-1,4-benzoquinone monoketals. Seven examples of this procedure are reported as is the conversion of 3-iodo-4,4-dimethoxycyclohexa-2,5-dienone into the natural product, (-)-harveynone. (C) 2010 Elsevier Ltd. All rights reserved.

KW - ANODIC-OXIDATION

KW - ABSOLUTE-CONFIGURATION

KW - EFFICIENT

KW - CYCLOHEXA-2,5-DIENONES

KW - (+)-PANEPOPHENANTHRIN

KW - (-)-TRICHOLOMENYN

KW - (+)-EPIEPOFORMIN

KW - (+)-OTTELIONE-A

KW - ASSIGNMENT

KW - PHENOLS

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U2 - 10.1016/j.tetlet.2010.10.047

DO - 10.1016/j.tetlet.2010.10.047

M3 - Article

SN - 0040-4039

VL - 51

SP - 6619

EP - 6621

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

A double oxidation procedure for the preparation of halogen-substituted para-benzoquinone monoketals: asymmetric synthesis of (-)-harveynone

Abstract

Keywords

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