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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• 作者：Harriet L. Newson ; Duncan A. Wild ; Sing Yee Yeung ; Brian W. Skelton ; Gavin R. Flematti ; Jane E. Allan ; Matthew J. Piggott
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：April 15, 2016
• 年：2016
• 卷：81
• 期：8
• 页码：3127-3135
• 全文大小：523K
• 年卷期：0
• ISSN：1520-6904

文摘

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 αD-line.