Access to 1,2,3,4-Tetraoxygenated Benzenes via a Double Baeyer-Villiger Reaction of Quinizarin Dimethyl Ether: Application to the Synthesis of Bioactive Natural Products from Antrodia camphorata

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Abstract

© 2016 American Chemical Society. The first systematic investigation into the Baeyer-Villiger reaction of an anthraquinone is presented. The double Baeyer-Villiger reaction of quinizarin dimethyl ether is viable, directly providing the dibenzo[b,f][1,4]-dioxocin-6,11-dione ring-system, which is otherwise difficult to prepare. This methodology provides rapid access to 1,2,3,4-tetraoxygenated benzenes, and has been exploited by application to the total synthesis of a natural occurring benzodioxole and its biphenyl dimer, which both display noteworthy biological activity. Interestingly, the axially chiral biphenyl was found to be configurationally stable, but the resolved enantiomers exhibit no optical activity at the aD-line.
Original languageEnglish
Pages (from-to)3127-3135
Number of pages9
JournalJournal of Organic Chemistry
Volume81
Issue number8
DOIs
Publication statusPublished - 2016

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Benzene
Biological Products
Anthraquinones
Enantiomers
Bioactivity
Dimers
diphenyl
dimethyl ether
1,4-dihydroxyanthraquinone

Cite this

@article{83e2669cb7374675895e3b114cff7ec8,
title = "Access to 1,2,3,4-Tetraoxygenated Benzenes via a Double Baeyer-Villiger Reaction of Quinizarin Dimethyl Ether: Application to the Synthesis of Bioactive Natural Products from Antrodia camphorata",
abstract = "{\circledC} 2016 American Chemical Society. The first systematic investigation into the Baeyer-Villiger reaction of an anthraquinone is presented. The double Baeyer-Villiger reaction of quinizarin dimethyl ether is viable, directly providing the dibenzo[b,f][1,4]-dioxocin-6,11-dione ring-system, which is otherwise difficult to prepare. This methodology provides rapid access to 1,2,3,4-tetraoxygenated benzenes, and has been exploited by application to the total synthesis of a natural occurring benzodioxole and its biphenyl dimer, which both display noteworthy biological activity. Interestingly, the axially chiral biphenyl was found to be configurationally stable, but the resolved enantiomers exhibit no optical activity at the aD-line.",
author = "Newson, {Harriet L.} and Wild, {Duncan A.} and S.Y. Yeung and Skelton, {Brian W.} and Flematti, {Gavin R.} and Allan, {Jane E.} and Piggott, {Matthew J.}",
year = "2016",
doi = "10.1021/acs.joc.5b02861",
language = "English",
volume = "81",
pages = "3127--3135",
journal = "The Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "8",

}

TY - JOUR

T1 - Access to 1,2,3,4-Tetraoxygenated Benzenes via a Double Baeyer-Villiger Reaction of Quinizarin Dimethyl Ether: Application to the Synthesis of Bioactive Natural Products from Antrodia camphorata

AU - Newson, Harriet L.

AU - Wild, Duncan A.

AU - Yeung, S.Y.

AU - Skelton, Brian W.

AU - Flematti, Gavin R.

AU - Allan, Jane E.

AU - Piggott, Matthew J.

PY - 2016

Y1 - 2016

N2 - © 2016 American Chemical Society. The first systematic investigation into the Baeyer-Villiger reaction of an anthraquinone is presented. The double Baeyer-Villiger reaction of quinizarin dimethyl ether is viable, directly providing the dibenzo[b,f][1,4]-dioxocin-6,11-dione ring-system, which is otherwise difficult to prepare. This methodology provides rapid access to 1,2,3,4-tetraoxygenated benzenes, and has been exploited by application to the total synthesis of a natural occurring benzodioxole and its biphenyl dimer, which both display noteworthy biological activity. Interestingly, the axially chiral biphenyl was found to be configurationally stable, but the resolved enantiomers exhibit no optical activity at the aD-line.

AB - © 2016 American Chemical Society. The first systematic investigation into the Baeyer-Villiger reaction of an anthraquinone is presented. The double Baeyer-Villiger reaction of quinizarin dimethyl ether is viable, directly providing the dibenzo[b,f][1,4]-dioxocin-6,11-dione ring-system, which is otherwise difficult to prepare. This methodology provides rapid access to 1,2,3,4-tetraoxygenated benzenes, and has been exploited by application to the total synthesis of a natural occurring benzodioxole and its biphenyl dimer, which both display noteworthy biological activity. Interestingly, the axially chiral biphenyl was found to be configurationally stable, but the resolved enantiomers exhibit no optical activity at the aD-line.

U2 - 10.1021/acs.joc.5b02861

DO - 10.1021/acs.joc.5b02861

M3 - Article

VL - 81

SP - 3127

EP - 3135

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

SN - 0022-3263

IS - 8

ER -