Rhodium-Catalyzed [3+2]-Annulation of ortho-Diazoquinones with Enol Ethers: Diversity-Oriented Total Synthesis of Aflatoxin B2

被引：8

作者：

Paymode, Dinesh J. ^{[1
,2
]}

Sharma, Indrajeet ^{[1
,2
]}

机构：

[1] Univ Oklahoma, Dept Chem & Biochem, 101 Stephenson Pkwy, Norman, OK 73019 USA

[2] Univ Oklahoma, Inst Nat Prod Applicat & Res Technol, 101 Stephenson Pkwy, Norman, OK 73019 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 2021卷 / 13期

基金：

美国国家科学基金会;

关键词：

Aflatoxin B-2; 3+2]-Annulation; Diazoquinones; 2; 3-Dihydrobenzofurans; Rhodium carbenoid; ENANTIOSELECTIVE TOTAL-SYNTHESIS; FORMAL SYNTHESIS; INTERMOLECULAR CARBOETHERIFICATION; CYCLOADDITION; CHEMISTRY; BIOLOGY; CASCADE;

D O I：

10.1002/ejoc.202100186

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient approach for synthesizing substituted and fused polycyclic 2,3-dihydrobenzofurans has been developed through a Rh-catalyzed [3+2]-annulation of ortho-diazoquinones with enol ethers. This methodology has a broad substrate scope and has been employed for the concise total synthesis of natural product aflatoxin B-2.

引用

页码：2034 / 2040

页数：7

共 50 条

[1] Intriguing formal [2+3] cycloaddition promoted by a hypervalent iodine reagent [J].

Berard, Didier ;

Giroux, Marc-Andre ;

Racicot, Leanne ;

Sabot, Cyrille ;

Canesi, Sylvain .

TETRAHEDRON, 2008, 64 (32) :7537-7544

[2] Regioselective Synthesis of Bicyclic and Polycyclic Systems by Cycloaddition Reactions of Alkenyl p-Benzoquinones [J].

Bisht, Shweta ;

Rani, Rashmi ;

Peddinti, Rama Krishna .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (01) :75-84

[3] Mechanistic Investigation of the Pd-Catalyzed Intermolecular Carboetherification and Carboamination of 2,3-Dihydrofuran: Similarities, Differences, and Evidence for Unusual Reaction Intermediates [J].

Borrajo-Calleja, Gustavo M. ;

Bizet, Vincent ;

Besnard, Celine ;

Mazet, Clement .

ORGANOMETALLICS, 2017, 36 (18) :3553-3563

[4] Palladium-Catalyzed Enantioselective Intermolecular Carboetherification of Dihydrofurans [J].

Borrajo-Calleja, Gustavo M. ;

Bizet, Vincent ;

Mazet, Clement .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (12) :4014-4017

[5] Chemistry and Biology of Mycotoxins and Related Fungal Metabolites [J].

Braese, Stefan ;

Encinas, Arantxa ;

Keck, Julia ;

Nising, Carl F. .

CHEMICAL REVIEWS, 2009, 109 (09) :3903-3990

[6]

Brase S., 2013, Chemistry of Mycotoxins, DOI [10.1007/978-3-7091-1312-7_14, DOI 10.1007/978-3-7091-1312-7_14]

[7]

BUCHI G, 1971, J AM CHEM SOC, V93, P746, DOI 10.1021/ja00732a032

[8] SYNTHESES OF TETRAHYDROFURO[2,3-B]BENZOFURANS - A SYNTHESIS OF (H-AFLATOXIN-B2 [J].

CASTELLINO, AJ ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (07) :1006-1011

[9] A serendipitous cascade of rhodium vinylcarbenoids with aminochalcones for the synthesis of functionalized quinolines [J].

Chinthapally, Kiran ;

Massaro, Nicholas P. ;

Padgett, Haylee L. ;

Sharma, Indrajeet .

CHEMICAL COMMUNICATIONS, 2017, 53 (90) :12205-12208

[10] Rhodium Carbenoid Initiated O-H Insertion/Aldol/Oxy-Cope Cascade for the Stereoselective Synthesis of Functionalized Oxacycles [J].

Chinthapally, Kiran ;

Massaro, Nicholas P. ;

Sharma, Indrajeet .

ORGANIC LETTERS, 2016, 18 (24) :6340-6343

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