Recent applications of the hetero Diels-Alder reaction in the total synthesis of natural products

被引:106
作者
Heravi, Majid M. [1 ]
Ahmadi, Tahereh [1 ]
Ghavidel, Mahdieh [1 ]
Heidari, Bahareh [1 ]
Hamidi, Hoda [1 ]
机构
[1] Alzahra Univ, Dept Chem, Tehran, Iran
基金
美国国家科学基金会;
关键词
ENANTIOSELECTIVE TOTAL-SYNTHESIS; FORMAL TOTAL-SYNTHESIS; POLYHYDROXYLATED NORTROPANE DERIVATIVES; STEREOSELECTIVE TOTAL-SYNTHESIS; ASYMMETRIC TOTAL SYNTHESES; STEREOCONTROLLED TOTAL-SYNTHESIS; RUTHENIUM-CATALYZED HYDRATION; OCCURRING TERPENE DERIVATIVES; SPONGE AGELAS-DENDROMORPHA; CONCISE TOTAL-SYNTHESIS;
D O I
10.1039/c5ra17488k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthetic utility and potential power of the Diels-Alder (D-A) reaction in organic chemistry is evident. These significances have been extended to the synthesis of a plethora and wide variety of heterocyclic compounds via [4 + 2] cycloaddition reactions, the so called hetero Diels-Alder (HDA) reaction. In this work we try to focus on the scope and preparative synthetic applications of the HDA reaction as a key step in the total synthesis of natural products.
引用
收藏
页码:101999 / 102075
页数:77
相关论文
共 587 条
[1]   First total synthesis of the marine alkaloids (±)-fasicularin and (±)-lepadiformine based on stereocontrolled intramolecular acylnitroso-Diels-Alder reaction [J].
Abe, H ;
Aoyagi, S ;
Kibayashi, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (19) :4583-4592
[2]   Bolivianine, a new sesterpene with an unusual skeleton from Hedyosmum angustifolium, and its isomer, isobolivianine [J].
Acebey, Lucia ;
Sauvain, Michel ;
Beck, Stephan ;
Moulis, Claude ;
Gimenez, Aberto ;
Jullian, Valerie .
ORGANIC LETTERS, 2007, 9 (23) :4693-4696
[3]   Anti-Leishmanial Lindenane Sesquiterpenes from Hedyosmum angustifolium [J].
Acebey, Lucia ;
Jullian, Valerie ;
Sereno, Denis ;
Chevalley, Severine ;
Estevez, Yannick ;
Moulis, Claude ;
Beck, Stephan ;
Valentin, Alex ;
Gimenez, Alberto ;
Sauvain, Michel .
PLANTA MEDICA, 2010, 76 (04) :365-U61
[4]  
AHLUWALIA VK, 1988, INDIAN J CHEM B, V27, P238
[5]   Convergent synthesis of the C31-C46 domain of the phorboxazole natural products [J].
Ahmed, F ;
Forsyth, CJ .
TETRAHEDRON LETTERS, 1998, 39 (3-4) :183-186
[6]   TRANSFORMATION OF INDOLE ALKALOIDS .1. CONVERSION OF OXINDOLE ALKALOIDS INTO INDOLE ALKALOIDS [J].
AIMI, N ;
YAMANAKA, E ;
ENDO, J ;
SAKAI, S ;
HAGINIWA, J .
TETRAHEDRON, 1973, 29 (14) :2015-2021
[7]  
Alcantara A. F. de C., 2000, Fitoterapia, V71, P613, DOI 10.1016/S0367-326X(00)00196-9
[8]   Antiproliferative activity of diarylheptanoids from the seeds of Alpinia blepharocalyx [J].
Ali, MS ;
Banskota, AH ;
Tezuka, Y ;
Saiki, I ;
Kadota, S .
BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2001, 24 (05) :525-528
[9]   GONIOTRIOL FROM GONIOTHALAMUS-GIGANTEUS [J].
ALKOFAHI, A ;
MA, WW ;
MCKENZIE, AT ;
BYRN, SR ;
MCLAUGHLIN, JL .
JOURNAL OF NATURAL PRODUCTS, 1989, 52 (06) :1371-1373
[10]   Intramolecular [4+2] cycloadditions of iminoacetonitriles: A new class of azadienophiles for hetero Diels-Alder reactions [J].
Amos, DT ;
Renslo, AR ;
Danheiser, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (17) :4970-4971