Cascade reaction based synthetic strategies targeting biologically intriguing indole polycycles

被引:81
作者
Ciulla, Maria Gessica [1 ]
Zimmermann, Stefan [1 ,2 ]
Kumar, Kamal [1 ]
机构
[1] Max Planck Inst Mol Physiol, Abt Chem Biol, Otto Hahn Str 11, D-44227 Dortmund, Germany
[2] Tech Univ Dortmund, Fak Chem & Chem Biol, Otto Hahn Str 6, D-44221 Dortmund, Germany
关键词
INTRAMOLECULAR DIELS-ALDER/1,3-DIPOLAR CYCLOADDITION; ONE-POT SYNTHESIS; NATURAL-PRODUCTS; DIELS-ALDER; DOMINO REACTIONS; DIVERGENT SYNTHESIS; BRANCHING CASCADES; CATALYTIC APPROACH; AZOMETHINE YLIDES; SYNTHESIS YIELDS;
D O I
10.1039/c8ob02620c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Indole polycycles are common structural frameworks of biologically intriguing small molecules of natural and synthetic origin and therefore remain interesting and challenging synthetic targets. Cascade reactions wherein a number of reactions occur in a sequential manner in the same reaction apparatus are highly efficient chemical processes which quickly build up molecular complexity. Synthetic approaches based on cascade reactions are highly useful as they tend to avoid multiple reaction work-up steps as well as purifications of all intermediary products. Therefore, in the last decade, a number of cascade reaction based approaches to build various molecular scaffolds of biological interest have been reported. However, a relatively smaller number of cascade reaction based synthetic strategies have targeted the indole polycycles. In this article, we have summarized some interesting cascade reaction based synthesis designs leading to complex indole polycycles including some biologically intriguing and natural product inspired indole frameworks.
引用
收藏
页码:413 / 431
页数:19
相关论文
共 128 条
[41]   Multi-Bond Forming Processes in Efficient Synthesis [J].
Green, Nicholas J. ;
Sherburn, Michael S. .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2013, 66 (03) :267-283
[42]   Redox-Neutral Indole Annulation Cascades [J].
Haibach, Michael C. ;
Deb, Indubhusan ;
De, Chandra Kanta ;
Seidel, Daniel .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (07) :2100-2103
[43]   SYSTEMATIC SYNTHESIS DESIGN .4. NUMERICAL CODIFICATION OF CONSTRUCTION REACTIONS [J].
HENDRICKSON, JB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (20) :5784-5800
[44]   Simple indole alkaloids and those with a nonrearranged monoterpenoid unit [J].
Higuchi, Kazuhiro ;
Kawasaki, Tomomi .
NATURAL PRODUCT REPORTS, 2007, 24 (04) :843-868
[45]   Recent Advances in Asymmetric Organocatalytic Construction of 3,3′-Spirocyclic Oxindoles [J].
Hong, Liang ;
Wang, Rui .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (06) :1023-1052
[46]   The combinatorial synthesis of bicyclic privileged structures or privileged substructures [J].
Horton, DA ;
Bourne, GT ;
Smythe, ML .
CHEMICAL REVIEWS, 2003, 103 (03) :893-930
[47]   Chemical biology -: identification of small molecule modulators of cellular activity by natural product inspired synthesis [J].
Huebel, Katja ;
Lessmann, Torben ;
Waldmann, Herbert .
CHEMICAL SOCIETY REVIEWS, 2008, 37 (07) :1361-1374
[48]   Transition-Metal-Catalyzed C-H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds [J].
Hummel, Joshua R. ;
Boerth, Jeffrey A. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2017, 117 (13) :9163-9227
[49]   Cascade reactions for syntheses of heterocycles [J].
Ihara, Masataka .
ARKIVOC, 2006, :416-438
[50]   Total Synthesis of (-)- and ent-(+)-Vindoline and Related Alkaloids [J].
Ishikawa, Hayato ;
Elliott, Gregory I. ;
Velcicky, Juraj ;
Choi, Younggi ;
Boger, Dale L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (32) :10596-10612