Tetrahedron Letters

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

DR Hookins, RJK Taylor

Index: Hookins, Daniel R.; Taylor, Richard J.K. Tetrahedron Letters, 2010 , vol. 51, # 50 p. 6619 - 6621

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Citation Number: 14

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.

 Related Synthetic Route
Methanol Structure

67-56-1

Methanol

2-Chlorophenol Structure

95-57-8

2-Chlorophenol

~65%

2-chloro-4,4-dimethoxycyclohexa-2,5-dien-1-one Structure

57197-15-6

2-chloro-4,4-di...

Methanol Structure

67-56-1

Methanol

2-Bromophenol Structure

95-56-7

2-Bromophenol

~51%

2-bromo-4,4-dimethoxycyclohexa-2,5-dien-1-one Structure

57197-16-7

2-bromo-4,4-dim...

Methanol Structure

67-56-1

Methanol

3-Chlorophenol Structure

108-43-0

3-Chlorophenol

~37%

3-chloro-4,4-dimethoxycyclohexa-2,5-dien-1-one Structure

119927-90-1

3-chloro-4,4-di...


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