C-H functionalization logic in total synthesis

被引:1135
作者
Gutekunst, Will R. [1 ]
Baran, Phil S. [1 ]
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
关键词
ENANTIOSELECTIVE TOTAL-SYNTHESIS; (+/-)-PENTALENOLACTONE-E METHYL-ESTER; ENANTIOSPECIFIC TOTAL-SYNTHESIS; BOND ACTIVATION; ORGANIC-SYNTHESIS; CELOGENTIN C; INTRAMOLECULAR ALKYLATION; PHOTOCHEMICAL REACTION; NOMINAL DIAZONAMIDES; EUDESMANE TERPENES;
D O I
10.1039/c0cs00182a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this critical review, the strategic and economic benefits of C-H functionalization logic will be analyzed through the critical lens of total synthesis. In order to illustrate the dramatically simplifying effects this type of logic can potentially have on synthetic planning, we take the reader through a series of case studies in which it has already been successfully applied. In the first section, a chronological look at key historical syntheses will be examined, leading into modern day examples. In the second section, our own experience with applying and executing synthesis with a C-H functionalization "mindset'' will be discussed (114 references).
引用
收藏
页码:1976 / 1991
页数:16
相关论文
共 118 条
[61]   Total synthesis of (-)-rhazinilam: Asymmetric C-H bond activation via the use of a chiral auxiliary [J].
Johnson, JA ;
Ning, L ;
Sames, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (24) :6900-6903
[62]   C-H bond activation of hydrocarbon segments in complex organic molecules: Total synthesis of the antimitotic rhazinilam [J].
Johnson, JA ;
Sames, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (26) :6321-6322
[63]   TOTAL SYNTHESIS OF SESQUITERPENOID ISHWARANE - STRUCTURE OF ISHWARONE [J].
KELLY, RB ;
ZAMECNIK, J ;
BECKETT, BA .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (10) :479-&
[64]   THE REACTIONS OF TERT-BUTYL PERBENZOATE AND OLEFINS - A STEREOSPECIFIC REACTION [J].
KHARASCH, MS ;
SOSNOVSKY, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (03) :756-756
[65]   Total Synthesis of (+)-11,11′-Dideoxyverticillin A [J].
Kim, Justin ;
Ashenhurst, James A. ;
Movassaghi, Mohammad .
SCIENCE, 2009, 324 (5924) :238-241
[66]   On the structure of Palau'amine: Evidence for the revised relative configuration from chemical synthesis [J].
Lanman, Brian A. ;
Overman, Larry E. ;
Paulini, Ralph ;
White, Nicole S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (42) :12896-12900
[67]   Synthesis of the Leu-Trp Component of the Celogentin Family of Cyclic Peptides Through a C-H Activation-Cross-Coupling Strategy [J].
Li, Barbara T. Y. ;
White, Jonathan M. ;
Hutton, Craig A. .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2010, 63 (03) :438-444
[68]  
Li J, 2001, ANGEW CHEM INT EDIT, V40, P4765, DOI 10.1002/1521-3773(20011217)40:24<4765::AID-ANIE4765>3.0.CO
[69]  
2-1
[70]  
Li J, 2001, ANGEW CHEM INT EDIT, V40, P4770, DOI 10.1002/1521-3773(20011217)40:24<4770::AID-ANIE4770>3.0.CO