The synthesis of cycloalka[b]furans via an Au(I)-catalyzed tandem reaction of 3-yne-1,2-diols

被引:5
作者
Liu, Wei-Ting [1 ]
Xu, Zheng-Liang [1 ]
Mou, Xue-Qing [1 ]
Zhang, Bang-Hong [1 ]
Bao, Wen [1 ]
Wang, Shao-Hua [1 ,2 ,3 ]
Lee, Dongjun [1 ]
Lei, Lin-Sheng [1 ]
Zhang, Kun [2 ]
机构
[1] Lanzhou Univ, Sch Pharm, Lanzhou 730000, Peoples R China
[2] Wuyi Univ, Sch Chem & Environm Engn, Jiangmen 529020, Peoples R China
[3] Sichuan Univ, Minist Educ, Key Lab Drug Targeting & Drug Delivery Syst, Chengdu, Peoples R China
关键词
HIGHLY SUBSTITUTED FURANS; BAND-GAP POLYMERS; ELECTROPHILIC CYCLIZATION; MULTISUBSTITUTED FURANS; EFFICIENT SYNTHESIS; CARBOXYLIC-ACIDS; NATURAL-PRODUCTS; GOLD CATALYSIS; MODULAR ENTRY; 2-(1-ALKYNYL)-2-ALKEN-1-ONES;
D O I
10.1039/c7ob01179b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An Au(I)-catalyzed cyclization/1,2-rearrangement/aromatization cascade of 3-yne-1,2-diols has been successfully realized. This reaction not only provides a new and efficient strategy for the synthesis of substituted cycloalka[b]furan compounds as well as their derivatives, but might also facilitate related biological studies.
引用
收藏
页码:6333 / 6337
页数:5
相关论文
共 84 条
[1]   An Eco-Friendly Scheme for the Cross-Linked Polybutadiene Elastomer via Thiol-Ene and Diels-Alder Click Chemistry [J].
Bai, Jing ;
Li, Hui ;
Shi, Zixing ;
Yin, Jie .
MACROMOLECULES, 2015, 48 (11) :3539-3546
[2]   Fungal metabolite ophiobolin A as a promising anti-glioma agent: In vivo evaluation, structure-activity relationship and unique pyrrolylation of primary amines [J].
Dasari, Ramesh ;
Masi, Marco ;
Lisy, Romana ;
Ferderin, Marlene ;
English, Lance R. ;
Cimmino, Alessio ;
Mathieu, Veronique ;
Brenner, Andrew J. ;
Kuhn, John G. ;
Whitten, Steven T. ;
Evidente, Antonio ;
Kiss, Robert ;
Kornienko, Alexander .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (20) :4544-4548
[3]   Ag(I)-catalyzed intramolecular transannulation of enynone tethered donor-acceptor cyclopropanes: a new synthesis of 2,3-dihydronaphtho[1,2-b]furans [J].
Dawande, Sudam Ganpat ;
Harode, Mandeep ;
Kalepu, Jagadeesh ;
Katukojvala, Sreenivas .
CHEMICAL COMMUNICATIONS, 2016, 52 (94) :13699-13701
[4]   Cycloadditions in Modern Polymer Chemistry [J].
Delaittre, Guillaume ;
Guimard, Nathalie K. ;
Barner-Kowollik, Christopher .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (05) :1296-1307
[5]   Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity [J].
Dorel, Ruth ;
Echavarren, Antonio M. .
CHEMICAL REVIEWS, 2015, 115 (17) :9028-9072
[6]   Spiro-Pyrrolidine-Catalyzed Asymmetric Conjugate Addition of Hydroxylamine to Enals and 2,4-Dienals [J].
Dou, Qing-Yun ;
Tu, Yong-Qiang ;
Zhang, Ye ;
Tian, Jin-Miao ;
Zhang, Fu-Min ;
Wang, Shao-Hua .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (06) :874-879
[7]   Copper(I)-Catalyzed A3-Coupling Based Reaction of Alkynes, Aldehydes, and Amines: An Efficient Approach to 2,5-Polysubstituted Dihydrofurans and 2,5-Disubstituted Furans [J].
Fan, Wu ;
Ma, Shengming .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (16) :3531-3539
[8]  
Fang H. B., 2013, ADV MAT RES, V746, P35
[9]   Synthesis, Structure and H+/K+-ATPase Inhibitory Activity of Novel Triazolyl Substituted Tetrahydrobenzofuran Derivatives via One-pot Three-component Click Reaction [J].
Fang, Hubiao ;
Jin, Lei ;
Huang, Nianyu ;
Wang, Junzhi ;
Zou, Kun ;
Luo, Zaigang .
CHINESE JOURNAL OF CHEMISTRY, 2013, 31 (06) :831-836
[10]   Molecular Complexity from Polyunsaturated Substrates: The Gold Catalysis Approach [J].
Fensterbank, Louis ;
Malacria, Max .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (03) :953-965