Sequential Assembly of Morita-Baylis-Hillman Carbonates and Activated ortho-Vinylbenzaldehydes To Construct Chiral Methanobenzo[7]annulenone Frameworks

被引：33
作者：
Jiang, Bo [1 ,2 ]
Xiao, Ben-Xian [1 ,2 ]
Ouyang, Qin [3 ,4 ]
Liang, Hua-Ping [3 ,4 ]
Du, Wei [1 ,2 ]
Chen, Ying-Chun [1 ,2 ,3 ,4 ]
机构：
[1] Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Minist Educ, Chengdu 610041, Sichuan, Peoples R China
[2] Sichuan Univ, Sichuan Res Ctr Drug Precis Ind Technol, West China Sch Pharm, Chengdu 610041, Sichuan, Peoples R China
[3] Third Mil Med Univ, State Key Lab Trauma Burn & Combined Injury, Chongqing 400038, Peoples R China
[4] Third Mil Med Univ, Coll Pharm, Chongqing 400038, Peoples R China
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 09期
关键词：
ENANTIOSELECTIVE SYNTHESIS; 3+2 ANNULATIONS; SKELETON; HOPEAHAINOL; QUATERNARY; HOPEANOL; ADDUCTS; ACCESS; DIMERS;
D O I：
10.1021/acs.orglett.9b01058
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The alpha-regioselective asymmetric [3 + 2] annulation reaction of Morita-Baylis-Hillman carbonates from isatins and activated ortho-vinylbenzaldehyses was developed by the catalysis of a chiral tertiary amine. The sequential N-heterocyclic carbene-mediated intramolecular Stetter reaction was conducted to finally furnish the bridged 5,8-methanobenzo [7] annulen-9-one architectures incorporating a spirooxindole motif with excellent stereoselectivity.
引用
收藏
页码：3310 / 3313
页数：4
相关论文
共 58 条
[1]   Toward Naphthocyclinones: Doubly Connected Octaketide Dimers with a Bicyclo[3.2.1]octadienone Core by Thiolate-Mediated Cyclization [J].
Ando, Yoshio ;
Hori, Subaru ;
Fukazawa, Takumi ;
Ohmori, Ken ;
Suzuki, Keisuke .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (33) :9650-9653
[2]   Catalytic Asymmetric Conjugate Addition of Nitroalkanes to 4-Nitro-5-styrylisoxazoles [J].
Baschieri, Andrea ;
Bernardi, Luca ;
Ricci, Alfredo ;
Suresh, Surisetti ;
Adamo, Mauro F. A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) :9342-9345
[3]   Enantioselective synthesis of nicotinic receptor probe 7,8-difluoro-1,2,3,4,5,6-hexahydro-1,5-methano-3-benzazocine [J].
Bashore, Crystal G. ;
Vetelino, Michael G. ;
Wirtz, Michael C. ;
Brooks, Paige R. ;
Frost, Heather N. ;
McDermott, Ruth E. ;
Whritenour, David C. ;
Ragan, John A. ;
Rutherford, Jennifer L. ;
Makowski, Teresa W. ;
Brenek, Steven J. ;
Coe, Jotham W. .
ORGANIC LETTERS, 2006, 8 (26) :5947-5950
[4]   Marine natural products [J].
Blunt, John W. ;
Carroll, Anthony R. ;
Copp, Brent R. ;
Davis, Rohan A. ;
Keyzers, Robert A. ;
Prinsep, Michele R. .
NATURAL PRODUCT REPORTS, 2018, 35 (01) :8-53
[5]   Cupreines and cupreidines: an established class of bifunctional cinchona organocatalysts [J].
Bryant, Laura A. ;
Fanelli, Rossana ;
Cobb, Alexander J. A. .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 :429-443
[6]   New Duclauxamide from Penicillium manginii YIM PH30375 and Structure Revision of the Duclauxin Family [J].
Cao, Pei ;
Yang, Jing ;
Miao, Cui-Ping ;
Yan, Yijun ;
Ma, Ya-Tuan ;
Li, Xiao-Nian ;
Zhao, Li-Xing ;
Huang, Sheng-Xiong .
ORGANIC LETTERS, 2015, 17 (05) :1146-1149
[7]   Phosphine-Catalyzed Aza-MBH Reactions of Vinylpyridines: Efficient and Rapid Access to 2,3,5-Triarylsubstituted 3-Pyrrolines [J].
Chen, Jing ;
Li, Jianjun ;
Wang, Jiazhe ;
Li, Hao ;
Wang, Wei ;
Guo, Yuewei .
ORGANIC LETTERS, 2015, 17 (09) :2214-2217
[8]   SYNTHESIS OF CARBON-BRIDGED DIBENZAZOCINES AND DIBENZODIAZOCINES - REGIOCHEMICAL CONTROL ELEMENTS IN THE BECKMANN REARRANGEMENT [J].
CONFALONE, PN ;
HUIE, EM .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (01) :79-83
[9]   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
[10]   Synthesis of functionalized bicyclo[3.2.1]octanes and their multiple uses in organic chemistry [J].
Filippini, MH ;
Rodriguez, J .
CHEMICAL REVIEWS, 1999, 99 (01) :27-76
123456