Construction of Highly Functionalized Xanthones via Rh-Catalyzed Cascade C-H Activation/O-Annulation

被引：20

作者：

Nale, Sagar D. ^{[1
]}

Maiti, Debabrata ^{[2
]}

Lee, Yong Rok ^{[1
]}

机构：

[1] Yeungnam Univ, Sch Chem Engn, Gyongsan 38541, South Korea

[2] Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 07期

基金：

新加坡国家研究基金会;

关键词：

NATURAL-PRODUCTS; ROOT BARK; SALICYLALDEHYDES; BIOSYNTHESIS; CONSTITUENTS; DERIVATIVES; ALDEHYDES; CHROMONES; ALKYNES; FRUITS;

D O I：

10.1021/acs.orglett.1c00391

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and efficient strategy for obtaining functionalized and multihydroxylated xanthones via Rh catalysis under redox-neutral conditions is developed. Diverse salicylaldehydes bearing heterocycles, aromatics, and fused aromatics can be rapidly coupled with 1,4-benzoquinones or 1,4-hydroquinones to afford valuable xanthones via cascade C-H/O-H functionalization and annulation. This protocol provides a rapid synthetic approach to obtain biologically active materials through late-stage functionalization and prepares natural products such as subelliptenone, pruniflorone N, and ravenelin.

引用

页码：2465 / 2470

页数：6

共 57 条

[1] Ru(II)-Catalyzed C-H activation and annulation of salicylaldehydes with monosubstituted and disubstituted alkynes [J].

Baruah, Swagata ;

Kaishap, Partha Pratim ;

Gogoi, Sanjib .

CHEMICAL COMMUNICATIONS, 2016, 52 (88) :13004-13007

[2] BIOSYNTHESIS OF FUNGAL XANTHONE RAVENELIN [J].

BIRCH, AJ ;

BALDAS, J ;

HLUBUCEK, JR ;

SIMPSON, TJ ;

WESTERMAN, PW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (08) :898-904

[3] Rh(iii)-Catalyzed C-H activation/annulation of salicylaldehydes with sulfoxonium ylides for the synthesis of chromones [J].

Cai, Libo ;

Zhu, Xiaoyi ;

Chen, Jiayi ;

Lin, Aijun ;

Yao, Hequan .

ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (21) :3688-3692

[4] A NEW XANTHONE AND ANTI-INFLAMMATORY CONSTITUENTS OF Garcinia subelliptica [J].

Chen, Jih-Jung ;

Hung, Ming-Chi ;

Liao, Hsiang-Ruei ;

Kuo, Yueh-Hsiung ;

Shu, Chih-Wen ;

Sung, Ping-Jyun ;

Lim, Yun-Ping ;

Kuo, Wen-Lung ;

Cheng, Lin-Yang ;

Wang, Sin-Ling ;

Wu, Jui-Jen .

CHEMISTRY OF NATURAL COMPOUNDS, 2017, 53 (04) :649-652

[5] Anti-inflammatory activity of mangostins from Garcinia mangostana [J].

Chen, Lih-Geeng ;

Yang, Ling-Ling ;

Wang, Ching-Chiung .

FOOD AND CHEMICAL TOXICOLOGY, 2008, 46 (02) :688-693

[6] Palladium-catalyzed cascade reactions of 3-iodochromones with aryl iodides and norbornadiene leading to annulated xanthones [J].

Cheng, Ming ;

Yan, Jianwei ;

Hu, Feng ;

Chen, Hong ;

Hu, Youhong .

CHEMICAL SCIENCE, 2013, 4 (01) :526-530

[7] Rh-Catalyzed Intramolecular Olefin Hydroacylation: Enantioselective Synthesis of Seven- and Eight-Membered Heterocycles [J].

Coulter, Matthew M. ;

Dornan, Peter K. ;

Dong, Vy M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (20) :6932-+

[8] C-H Activation: Toward Sustainability and Applications [J].

Dalton, Toryn ;

Faber, Teresa ;

Glorius, Frank .

ACS CENTRAL SCIENCE, 2021, 7 (02) :245-261

[9] On-Water Cp*Ir(III)-Catalyzed C-H Functionalization for the Synthesis of Chromones through Annulation of Salicylaldehydes with Diazo-Ketones [J].

Debbarma, Suvankar ;

Sk, Md Raja ;

Modak, Biswabrata ;

Maji, Modhu Sudan .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (10) :6207-6216

[10] Harnessing Stereospecific Z-Enamides through Silver-Free Cp*Rh(III) Catalysis by Using Isoxazoles as Masked Electrophiles [J].

Debbarma, Suvankar ;

Bera, Sourav Sekhar ;

Maji, Modhu Sudan .

ORGANIC LETTERS, 2019, 21 (03) :835-839

← 1 2 3 4 5 6 →