The Diels-Alder Reaction and its Applications in the Total Synthesis of Natural Products

被引:7
作者
Ran, Hongyu [1 ]
Huang, Gangliang [1 ]
机构
[1] Chongqing Normal Univ, Coll Chem, Chongqing 401331, Peoples R China
关键词
Diels-Alder reaction; Total synthesis; Applications; BOND FORMATION; CARPANONE;
D O I
10.2174/1570179413666160624111111
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Diels-Alder (DA) reaction has been applied to the total synthesis of natural products. It can get good yields because of high stereoselectivity and regioselectivity. Herein, the DA reaction catalyzed by Lewis acids was introduced, and some total syntheses of natural products from 2013 to 2015 using DA reaction were also illustrated and analyzed.
引用
收藏
页码:847 / 860
页数:14
相关论文
共 30 条
[1]   D, L-ISOCHRYSOHERMIDIN AND MESO-ISOCHRYSOHERMIDIN - TOTAL SYNTHESIS AND INTERSTRAND DNA CROSS-LINKING [J].
BOGER, DL ;
BALDINO, CM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) :11418-11425
[2]   Concise Total Synthesis of (-)-Auxofuran by a Click Diels-Alder Strategy [J].
Boukouvalas, John ;
Loach, Richard P. .
ORGANIC LETTERS, 2013, 15 (18) :4912-4914
[3]  
Carey F.A., 2009, ADV ORG CHEM, P848
[4]   TOTAL SYNTHESIS OF CARPANONE [J].
CHAPMAN, OL ;
ENGEL, MR ;
SPRINGER, JP ;
CLARDY, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (24) :6696-&
[5]   A new catalytic Cu(II)/Sparteine oxidant system for β,β-phenolic couplings of styrenyl phenols:: Synthesis of carpanone and unnatural analogs [J].
Daniels, R. Nathan ;
Fadeyi, Olugbeminiyi O. ;
Lindsley, Craig W. .
ORGANIC LETTERS, 2008, 10 (18) :4097-4100
[6]  
Diels O., 1928, LIEBIGS ANN CHEM, V460, P98
[7]   Enhancing reactivity of carbonyl compounds via hydrogen-bond formation.: A DFT study of the hetero-Diels-Alder reaction between butadiene derivative and acetone in chloroform [J].
Domingo, LR ;
Andrés, J .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (22) :8662-8668
[8]   A mechanistic study of the participation of azomethine ylides and carbonyl ylides in [3+2] cycloaddition reactions [J].
Domingo, Luis R. ;
Aurell, Maria J. ;
Perez, Patricia .
TETRAHEDRON, 2015, 71 (07) :1050-1057
[9]   A new C-C bond formation model based on the quantum chemical topology of electron density [J].
Domingo, Luis R. .
RSC ADVANCES, 2014, 4 (61) :32415-32428
[10]   Understanding the mechanism of non-polar Diels-Alder reactions. A comparative ELF analysis of concerted and stepwise diradical mechanisms [J].
Domingo, Luis R. ;
Chamorro, Eduardo ;
Perez, Patricia .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (24) :5495-5504