Applications of C-H Functionalization Logic to Cyclobutane Synthesis

被引:167
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
CATALYZED DIRECT ARYLATION; METHYLENE C(SP(3))-H BOND; MULTICOMPONENT REACTIONS; STRUCTURAL REVISION; SCALABLE SYNTHESIS; NATURAL-PRODUCTS; SOLID-STATE; ACID; ACTIVATION; AMIDES;
D O I
10.1021/jo4027148
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The application of C-H functionalization logic to target-oriented synthesis provides an exciting new venue for the development of new and useful strategies in organic chemistry. In this article, C-H functionalization reactions are explored as an alternative approach to access pseudodimeric cyclobutane natural products, such as the dictazole and the piperarborenine families. The use of these strategies in a variety of complex settings highlights the subtle geometric, steric, and electronic effects at play in the auxiliary guided C-H fimctionalization of cyclobutanes.
引用
收藏
页码:2430 / 2452
页数:23
相关论文
共 117 条
[11]   Synthesis and evaluation of the first cis-cyclobutane-containing receptor for lipid A [J].
Bucholtz, Kevin M. ;
Gareiss, Peter C. ;
Tajc, Stephen G. ;
Miller, Benjamin L. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (21) :3973-3979
[12]   Ketene-Based Route to rigid Cyclobutanediol Monomers for the Replacement of BPA in High Performance Polyesters [J].
Burke, Daniel J. ;
Kawauchi, Takehiro ;
Kade, Matthew J. ;
Leibfarth, Frank A. ;
McDearmon, Brenden ;
Wolffs, Martin ;
Kierstead, Paul H. ;
Moon, Bongjin ;
Hawker, Craig J. .
ACS MACRO LETTERS, 2012, 1 (11) :1228-1232
[13]   C-H Activation: A Complementary Tool in the Total Synthesis of Complex Natural Products [J].
Chen, David Y. -K. ;
Youn, So Won .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (31) :9452-9474
[14]   TOPOCHEMISTRY .1. SURVEY [J].
COHEN, MD ;
SCHMIDT, GMJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (JUN) :1996-+
[15]   TOPOCHEMISTRY .2. PHOTOCHEMISTRY OF TRANS-CINNAMIC ACIDS [J].
COHEN, MD ;
SCHMIDT, GMJ ;
SONNTAG, FI .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (JUN) :2000-&
[16]   INTERNAL PHOTOADDITION REACTIONS OF 2-PYRONE + N-METHYL-2-PYRIDONE - NEW SYNTHETIC APPROACH TO CYCLOBUTADIENE [J].
COREY, EJ ;
STREITH, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (05) :950-&
[17]   SYNTHETIC APPLICATIONS OF INTRAMOLECULAR ENONE OLEFIN PHOTOCYCLOADDITIONS [J].
CRIMMINS, MT .
CHEMICAL REVIEWS, 1988, 88 (08) :1453-1473
[18]   Pd(II)-Catalyzed ortho- or meta-C-H Olefination of Phenol Derivatives [J].
Dai, Hui-Xiong ;
Li, Gang ;
Zhang, Xing-Guo ;
Stepan, Antonia F. ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (20) :7567-7571
[19]   Dictazoles: Potential Vinyl Cyclobutane Biosynthetic Precursors to the Dictazolines [J].
Dai, Jingqiu ;
Jimenez, Jorge I. ;
Kelly, Michelle ;
Williams, Philip G. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (07) :2399-2402
[20]   STEREOSELECTIVE SYNTHESES VIA A PHOTOCHEMICAL TEMPLATE EFFECT [J].
DAMEN, J ;
NECKERS, DC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (09) :3265-3267