Diversity oriented microwave-assisted synthesis of (-)-Steganacin aza-analogues

被引:36
作者
Mont, Nuria [1 ]
Mehta, Vaibhav Pravinchandra [1 ]
Appukkuttan, Prasad [1 ]
Beryozkina, Tetyana
Toppet, Suzzane
Van Hecke, Kristof
Van Meervelt, Luc
Voet, Arnout
DeMaeyer, Marc
Van der Eycken, Erik [1 ]
机构
[1] Katholieke Univ Leuven, LOMAC, Dept Chem, B-3001 Louvain, Belgium
关键词
D O I
10.1021/jo801290j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A novel microwave-assisted, highly efficient protocol for the synthesis of hitherto unknown aza-analogues of (-)-Steganacin, a naturally occurring bisbenzocyclooctadiene lignan lactone with potent antileukemic and tubulin polymerization inhibitory activity, has been developed. Focused microwave irradiation is demonstrated to be highly beneficial in promoting the three crucial steps of the sequence to effect the final ring closure: the Suzuki-Miyaura reaction, Cu-mediated A(3)-coupling, as well as the intramolecular Huisgen 1,3-dipolar cycloaddition.
引用
收藏
页码:7509 / 7516
页数:8
相关论文
共 50 条
[21]   Synthesis of aza-analogues of the glycosylated tyrosine portion of mannopeptimycin-E [J].
Guppi, Sanjeeva R. ;
O'Doherty, George A. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (13) :4966-4969
[22]   AN EASY AND CONCISE SYNTHESIS OF AZA-ANALOGUES OF CALCIUM ANTAGONISTIC BENZOTHIAZOLE DERIVATIVES [J].
COUTURE, A ;
HUGUERRE, E ;
GRANDCLAUDON, P .
SYNTHETIC COMMUNICATIONS, 1989, 19 (3-4) :713-719
[23]   Synthesis of (±)-Pterocarpin and Its Thia- and Aza-Analogues in a Modular Manner [J].
Huang, Qingyun ;
Wang, Peng ;
Tian, Yu ;
Song, Ni ;
Ren, Sumei ;
Tao, Jiaxin ;
Hang, Kaini ;
Li, Ming .
SYNLETT, 2015, 26 (10) :1385-1390
[24]   Synthesis of ring-expanded aza-analogues of bisbenzocyclooctadiene lignan lactones [J].
Donets, Pavel A. ;
Van der Eycken, Erik V. .
QSAR & COMBINATORIAL SCIENCE, 2007, 26 (11-12) :1239-1242
[25]   A novel multicomponent microwave-assisted synthesis of 5-aza-adenines [J].
Dolzhenko, Anton V. ;
Kalinina, Svetlana A. ;
Kalinin, Dmitrii V. .
RSC ADVANCES, 2013, 3 (36) :15850-15855
[26]   Synthesis of peripherally substituted aza-analogues of Si(IV) phthalocyanines by complexation method [J].
Kolarova, Michaela ;
Zimcik, Petr ;
Ivanova, Svetlana ;
Miletin, Miroslav ;
Novakova, Veronika .
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2023, 27 (01) :444-451
[27]   An efficient Ugi-3CR/aza Diels-Alder/Pomeranz-Fritsch protocol towards novel aza-analogues of (±)-nuevamine, (±)-lennoxamine and magallanesine: a diversity oriented synthesis approach [J].
Vazquez-Vera, Oscar ;
Sanchez-Badillo, Jorge S. ;
Islas-Jacome, Alejandro ;
Renteria-Gomez, Manuel A. ;
Pharande, Shrikant G. ;
Cortes-Garcia, Carlos J. ;
Rincon-Guevara, Monica A. ;
Ibarra, Ilich A. ;
Gamez-Montano, Rocio ;
Gonzalez-Zamora, Eduardo .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (11) :2363-2369
[28]   Microwave-Assisted Solid Phase Synthesis of GLP-1-Analogues [J].
Chi, Yushi ;
Zhang, Huibin ;
Zhou, Jinpei ;
Huang, Wenlong ;
Ni, Shuaijian .
LETTERS IN ORGANIC CHEMISTRY, 2008, 5 (05) :399-402
[29]   Synthesis and antiprotozoal activity of dicationic 2,6-diphenylpyrazines and aza-analogues [J].
Hu, Laixing ;
Patel, Alpa ;
Bondada, Lavanya ;
Yang, Sihyung ;
Wang, Michael Zhuo ;
Munde, Manoj ;
Wilson, W. David ;
Wenzler, Tanja ;
Brun, Reto ;
Boykin, David W. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (21) :6732-6741
[30]   A CONVENIENT SYNTHESIS OF 9H-THIOXANTHEN-9-ONES AND THEIR AZA-ANALOGUES [J].
Kobayashi, Kazuhiro ;
Komatsu, Toshihide ;
Nakagawa, Kazuhiro ;
Hara, Erika ;
Yuba, Shohei .
HETEROCYCLES, 2013, 87 (12) :2577-2587