Recent Applications of Cyclopropane-Based Strategies to Natural Product Synthesis

被引：231
作者：
Tang, Pei [1 ]
Qin, Yong [1 ,2 ]
机构：
[1] Chongqing Univ, Coll Chem Chem Engn & Bioengn, Innovat Drug Res Ctr, Chongqing 401331, Peoples R China
[2] Sichuan Univ, W China Sch Pharm, Key Lab Drug Targeting & Novel Delivery Syst, Minist Educ, Chengdu 610041, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 19期
关键词：
cyclopropanes; cyclopropanation; ring opening; total synthesis; natural products; DONOR-ACCEPTOR CYCLOPROPANES; CATALYZED 5+2 CYCLOADDITIONS; 3+2 CROSS-CYCLOADDITION; FORMAL SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; ENE-VINYLCYCLOPROPANES; ORGANIC-SYNTHESIS; CONSTRUCTION; LEWIS; DERIVATIVES;
D O I：
10.1055/s-0032-1317011
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Activated cyclopropanes show versatile reactivity and are therefore powerful building blocks in organic chemistry and natural product synthesis. This review focuses on recent applications of cyclopropane-based approaches to the syntheses of natural products. These applications include diverse processes involving cyclopropanation-ring-opening-cyclization or ring expansion to form key natural product skeletons.
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收藏
页码：2969 / 2984
页数：16
相关论文
共 78 条
[1]   Synthetic studies on nemorosone via enantioselective intramolecular cyclopropanation [J].
Abe, Masahito ;
Saito, Aya ;
Nakada, Masahisa .
TETRAHEDRON LETTERS, 2010, 51 (09) :1298-1302
[2]  
[Anonymous], 2009, SYNTHESIS
[3]   Lewis Acid Catalyzed Intramolecular [4+2] and [3+2] Cross-Cycloaddition of Alkynylcyclopropane Ketones with Carbonyl Compounds and Imines [J].
Bai, Yu ;
Tao, Weijie ;
Ren, Jun ;
Wang, Zhongwen .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (17) :4112-4116
[4]   Thermal rearrangements of vinylcyclopropanes to cyclopentenes [J].
Baldwin, JE .
CHEMICAL REVIEWS, 2003, 103 (04) :1197-1212
[5]   The cycloaddition strategy for the synthesis of natural products containing carbocyclic seven-membered rings [J].
Battiste, MA ;
Pelphrey, PM ;
Wrightthl, DL .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (13) :3438-3447
[6]   Iron-Catalyzed [3+2] Annulation of Aminocyclopropanes with Aldehydes: Stereoselective Synthesis of Aminotetrahydrofurans [J].
Benfatti, Fides ;
de Nanteuil, Florian ;
Waser, Jerome .
ORGANIC LETTERS, 2012, 14 (01) :386-389
[7]   The total synthesis of (-)-connatusin A, a hirsutane-type sesquiterpene isolated from the fungus Lentinus connatus BCC8996 [J].
Bon, David J. -Y. D. ;
Banwell, Martin G. ;
Cade, Ian A. ;
Willis, Anthony C. .
TETRAHEDRON, 2011, 67 (43) :8348-8352
[8]   A chemoenzymatic total synthesis of the hirsutene-type sesquiterpene (+)-connatusin B from toluene [J].
Bon, David J. -Y. D. ;
Banwell, Martin G. ;
Willis, Anthony C. .
TETRAHEDRON, 2010, 66 (39) :7807-7814
[9]   Heterocycles from alkylidenecyclopropanes [J].
Brandi, A ;
Cicchi, S ;
Cordero, FM ;
Goti, A .
CHEMICAL REVIEWS, 2003, 103 (04) :1213-1269
[10]   Asymmetric Synthesis of (+)-Polyanthellin A [J].
Campbell, Matthew J. ;
Johnson, Jeffrey S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (30) :10370-+
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