Total Synthesis of Naphterpin and Marinone Natural Products

被引：20

作者：

Murray, Lauren A. M. ^{[1
]}

Fallon, Thomas ^{[1
]}

Sumby, Christopher J. ^{[1
]}

George, Jonathan H. ^{[1
]}

机构：

[1] Univ Adelaide, Dept Chem, Adelaide, SA 5005, Australia

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 20期

基金：

澳大利亚研究理事会;

关键词：

STRUCTURAL ELUCIDATION; BIOMIMETIC SYNTHESIS; NAPHTHOQUINONES; MEROCHLORINS; BIOSYNTHESIS; ANTIBIOTICS;

D O I：

10.1021/acs.orglett.9b03095

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and divergent strategy for the synthesis of the naphterpin and marinone meroterpenoid families has been developed. The approach features a succession of pericyclic reactions-an aromatic Claisen rearrangement, a retro-6 pi-electrocyclization, and two Diels-Alder reactions-which facilitated the first total synthesis of naphterpin itself in five steps from 2,5-dimethoxyphenol, alongside similar syntheses of 7-demethylnaphterpin and debromomarinone. Late-stage oxidation and bromination reactions were also investigated, leading to the first total syntheses of naphterpins B and C and isomarinone.

引用

页码：8312 / 8315

页数：4

共 47 条

[1] Addition of silyloxydienes to 2,6-dibromo-1,4-benzoquinone: an approach to highly oxygenated bromonaphthoquinones for the synthesis of thysanone [J].

Barker, D ;

Brimble, MA ;

Do, P ;

Turner, P .

TETRAHEDRON, 2003, 59 (14) :2441-2449

[2] A Stereoselective Vanadium-Dependent Chloroperoxidase in Bacterial Antibiotic Biosynthesis [J].

Bernhardt, Peter ;

Okino, Tatsufumi ;

Winter, Jaclyn M. ;

Miyanaga, Akimasa ;

Moore, Bradley S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (12) :4268-4270

[3] Total Synthesis of (-)-Merochlorin A [J].

Brandstaetter, Marco ;

Freis, Manuel ;

Huwyler, Nikolas ;

Carreira, Erick M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (08) :2490-2494

[4] The importance of asking "how and why?" in natural product structure elucidation [J].

Brown, Patrick D. ;

Lawrence, Andrew L. .

NATURAL PRODUCT REPORTS, 2017, 34 (10) :1193-1202

[5] IDENTIFICATION AND CHARACTERIZATION OF NATURALLY-OCCURRING RUBIADINS [J].

COURCHESNE, M ;

BRASSARD, P .

JOURNAL OF NATURAL PRODUCTS, 1993, 56 (05) :722-730

[6] A Multitasking Vanadium-Dependent Chloroperoxidase as an Inspiration for the Chemical Synthesis of the Merochlorins [J].

Diethelm, Stefan ;

Teufel, Robin ;

Kaysser, Leonard ;

Moore, Bradley S. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (41) :11023-11026

[7] Developing a new resource for drug discovery: marine actinomycete bacteria [J].

Fenical, William ;

Jensen, Paul R. .

NATURE CHEMICAL BIOLOGY, 2006, 2 (12) :666-673

[8] Total synthesis of the cyclic monoterpenoid pyrano[3,2-a]carbazole alkaloids derived from 2-hydroxy-6-methylcarbazole [J].

Gassner, Cemena ;

Hesse, Ronny ;

Schmidt, Arndt W. ;

Knoelker, Hans-Joachim .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (33) :6490-6499

[9] The Diels-Alder Approach to Δ9-Tetrahydrocannabinol Derivatives [J].

Glaeser, Franziska ;

Broehmer, Manuel C. ;

Hurrle, Thomas ;

Nieger, Martin ;

Braese, Stefan .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (07) :1516-1524

[10] IMPROVED SYNTHESIS OF ARYL 1,1-DIMETHYLPROPARGYL ETHERS [J].

GODFREY, JD ;

MUELLER, RH ;

SEDERGRAN, TC ;

SOUNDARARAJAN, N ;

COLANDREA, VJ .

TETRAHEDRON LETTERS, 1994, 35 (35) :6405-6408

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