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

被引：10

作者：

Newson, Harriet L. ^{[1
]}

Wild, Duncan A. ^{[1
]}

Yeung, Sing Yee ^{[1
]}

Skelton, Brian W. ^{[2
]}

Flematti, Gavin R. ^{[1
]}

Allan, Jane E. ^{[3
]}

Piggott, Matthew J. ^{[1
]}

机构：

[1] Univ Western Australia, Sch Chem & Biochem, Perth, WA 6009, Australia

[2] Univ Western Australia, Ctr Microscopy Characterisat & Anal, Perth, WA 6009, Australia

[3] Univ Western Australia, Sch Med & Pharmacol, Perth, WA 6009, Australia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 08期

关键词：

BIARYL COUPLING REACTION; DERIVATIVES; EFFICIENT; DECARBONYLATION; OXIDATION; ALDEHYDES; PHENOLS; ANALOGS;

D O I：

10.1021/acs.joc.5b02861

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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[bf][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 alpha D-line.

引用

页码：3127 / 3135

页数：9

共 59 条

[1] Synthesis of methoxy-substituted phenols by peracid oxidation of the aromatic ring [J].

Bjorsvik, HR ;

Occhipinti, G ;

Gambarotti, C ;

Cerasino, L ;

Jensen, VR .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (18) :7290-7296

[2] ISOFRAXIDIN, A CYTO-TOXIC COUMARIN FROM MICRANDRA-ELATA (EUPHORBIACEAE) [J].

BORRIS, RP ;

CORDELL, GA ;

FARNSWORTH, NR .

JOURNAL OF NATURAL PRODUCTS, 1980, 43 (05) :641-643

[3] Ethynylbenzenoid metabolites of Antrodia camphorata: synthesis and inhibition of TNF expression [J].

Buccini, Marco ;

Punch, Kathryn A. ;

Kaskow, Belinda ;

Flematti, Gavin R. ;

Skelton, Brian W. ;

Abraham, Lawrence J. ;

Piggott, Matthew J. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (07) :1100-1113

[4] Some transformations of adducts of 3,6-dimethoxy-4,5-methylenedioxy-1,2-didehydrobenzene and furans. An approach to the 5,8-dimethoxy-6,7-methylenedioxynaphtho[2,3-c]furan-4,9-dione ring system of ventilone A [J].

Buttery, JH ;

Wege, D .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1998, 51 (05) :409-419

[5] REGIOSPECIFIC SYNTHESIS OF QUINIZARIN AND NAPHTHAZARIN DERIVATIVES BY CYCLOADDITION [J].

CAMERON, DW ;

FEUTRILL, GI ;

MCKAY, PG .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (10) :2095-2109

[6] A FACILE ROUTE TO PERYLENEQUINONE [J].

CHAO, C ;

ZHANG, P .

TETRAHEDRON LETTERS, 1988, 29 (02) :225-226

[7] Isolation and Synthesis of a Bioactive Benzenoid Derivative from the Fruiting Bodies of Antrodia camphorata [J].

Chen, Pi-Yu ;

Wu, Jen-Der ;

Tang, Kai-Yih ;

Yu, Chieh-Chou ;

Kuo, Yueh-Hsiung ;

Zhong, Wen-Bin ;

Lee, Ching-Kuo .

MOLECULES, 2013, 18 (07) :7600-7608

[8]

Cherkaoui MZ, 1997, NEW J CHEM, V21, P1203

[9]

CHIANG HC, 1995, PHYTOCHEMISTRY, V39, P613, DOI 10.1016/0031-9422(95)00025-3

[10] Steric Control of Site Selectivity in the Pd-Catalyzed C-H Acetoxylation of Simple Arenes [J].

Cook, Amanda K. ;

Emmert, Marion H. ;

Sanford, Melanie S. .

ORGANIC LETTERS, 2013, 15 (21) :5428-5431

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