Recent applications of C-H functionalization in complex natural product synthesis

被引:495
作者
Abrams, Dylan J. [1 ]
Provencher, Philip A. [1 ]
Sorensen, Erik J. [1 ]
机构
[1] Princeton Univ, Dept Chem, Princeton, NJ 08544 USA
基金
美国国家科学基金会;
关键词
ENANTIOSELECTIVE TOTAL-SYNTHESIS; CONCISE TOTAL-SYNTHESIS; ASYMMETRIC TOTAL-SYNTHESIS; AXIALLY CHIRAL BIARYLS; STEREOCHEMICAL ASSIGNMENT; ENANTIOSPECIFIC SYNTHESIS; SCALABLE SYNTHESIS; UNIFIED APPROACH; BOND ACTIVATION; C(SP(3))-H;
D O I
10.1039/c8cs00716k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this review, recent examples featuring C-H functionalization in the synthesis of complex natural products are discussed. A focus is given to the way in which C-H functionalization can influence the logical process of retrosynthesis, and the review is organized by the type and method of C-H functionalization.
引用
收藏
页码:8925 / 8967
页数:43
相关论文
共 160 条
[11]   A Unified Approach for the Enantioselective Synthesis of the Brominated Chamigrene Sesquiterpenes [J].
Burckle, Alexander J. ;
Vasilev, Vasil H. ;
Burns, Noah Z. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (38) :11476-11479
[12]   REACTIVITY OF ORGANOPHOSPHORUS COMPOUNDS .19. REDUCTION OF NITRO-COMPOUNDS BY TRIETHYL PHOSPHITE - A CONVENIENT NEW ROUTE TO CARBAZOLES INDOLES INDAZOLES TRIAZOLES AND RELATED COMPOUNDS [J].
CADOGAN, JIG ;
CAMERONW.M ;
MACKIE, RK ;
SEARLE, RJG .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (SEP) :4831-&
[13]   Catalytic Asymmetric Total Synthesis of (-)-Actinophyllic Acid [J].
Cai, Lingchao ;
Zhang, Kui ;
Kwon, Ohyun .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (10) :3298-3301
[14]   An unusual intramolecular Diels-Alder approach toward maoecrystal V [J].
Carberry, Patrick ;
Viernes, Dennis R. ;
Choi, Lydia B. ;
Fegley, Mark W. ;
Chisholm, John D. .
TETRAHEDRON LETTERS, 2013, 54 (13) :1734-1737
[15]  
Chan KSL, 2014, NAT CHEM, V6, P146, DOI [10.1038/NCHEM.1836, 10.1038/nchem.1836]
[16]   Enantioselective Total Synthesis of (+)-Psiguadial B [J].
Chapman, Lauren M. ;
Beck, Jordan C. ;
Wu, Linglin ;
Reisman, Sarah E. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (31) :9803-9806
[17]   A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis [J].
Chen, Mark S. ;
White, M. Christina .
SCIENCE, 2007, 318 (5851) :783-787
[18]  
Cherney EC, 2014, J AM CHEM SOC, V136, P12592, DOI [10.1021/ja507321J, 10.1021/ja507321j]
[19]   Intramolecular Oxidative C-N Bond Formation for the Synthesis of Carbazoles: Comparison of Reactivity between the Copper-Catalyzed and Metal-Free Conditions [J].
Cho, Seung Hwan ;
Yoon, Jungho ;
Chang, Sukbok .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) :5996-6005
[20]   Room-temperature enantioselective C-H iodination via kinetic resolution [J].
Chu, Ling ;
Xiao, Kai-Jiong ;
Yu, Jin-Quan .
SCIENCE, 2014, 346 (6208) :451-455