One-Pot Synthesis of Semi-Saturated Fused Polycyclic Iminosugars by a Diels-Alder Reaction

被引：1

作者：

Xie, Song ^{[1
]}

Wu, Jilai ^{[1
]}

Zhou, Likai ^{[1
,2
]}

Wei, Chao ^{[1
]}

Li, Xiaoliu ^{[1
]}

Chen, Hua ^{[1
]}

机构：

[1] Hebei Univ, Coll Chem & Mat Sci, Key Lab Chem Biol Hebei Prov, Baoding 071002, Hebei, Peoples R China

[2] Xingtai Univ, Coll Chem & Chem Engn, Xingtai 054001, Hebei, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 28卷 / 01期

基金：

中国国家自然科学基金;

关键词：

Polycyclic iminosugars; Diels-Alder reaction; One-pot processes; Stereoselectivity; Multicomponent reactions; BENZIMIDAZOLE-IMINOSUGARS; INHIBITORY-ACTIVITIES; DESIGN;

D O I：

10.1002/ejoc.202401005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of semi-saturated fused polycyclic iminosugars were synthesized by one-pot stereoselective three-component reactions of D-ribose tosylate, aniline and cycloenones under heating conditions. The N-aryl enamine derived from an iminium ion is the key intermediate for the reaction. In this way, various novel complex fused iminosugars were obtained through a normal Diels-Alder mechanism at 80 degrees C. This strategy will enable the preparation of bioactive iminosugar analogues with structural diversity.

引用

页数：8

共 45 条

[1] Structure-Based Drug Design of Novel Potent and Selective Tetrahydropyrazolo[1,5-a]pyrazines as ATR Inhibitors [J].

Barsanti, Paul A. ;

Aversa, Robert J. ;

Jin, Xianming ;

Pan, Yue ;

Lu, Yipin ;

Elling, Robert ;

Jain, Rama ;

Knapp, Mark ;

Lan, Jiong ;

Lin, Xiaodong ;

Rudewicz, Patrick ;

Sim, Janet ;

Taricani, Lorena ;

Thomas, George ;

Xiao, Linda ;

Yue, Qin .

ACS MEDICINAL CHEMISTRY LETTERS, 2015, 6 (01) :37-41

[2] Hydropyridylation of Olefins by Intramolecular Minisci Reaction [J].

Bordi, Samuele ;

Starr, Jeremy T. .

ORGANIC LETTERS, 2017, 19 (09) :2290-2293

[3] Property- and Structure-Guided Discovery of a Tetrahydroindazole Series of Interleukin-2 Inducible T-Cell Kinase Inhibitors [J].

Burch, Jason D. ;

Lau, Kevin ;

Barker, John J. ;

Brookfield, Fred ;

Chen, Yong ;

Chen, Yuan ;

Eigenbrot, Charles ;

Ellebrandt, Claire ;

Ismaili, M. Hicham A. ;

Johnson, Adam ;

Kordt, Daniel ;

MacKinnon, Colin H. ;

McEwan, Paul A. ;

Ortwine, Daniel F. ;

Stein, Daniel B. ;

Wang, Xiaolu ;

Winkler, Dirk ;

Yuen, Po-Wai ;

Zhang, Yamin ;

Zarrin, Ali A. ;

Pei, Zhonghua .

JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (13) :5714-5727

[4] Enantioselective Total Synthesis of (+)-Psiguadial B [J].

Chapman, Lauren M. ;

Beck, Jordan C. ;

Wu, Linglin ;

Reisman, Sarah E. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (31) :9803-9806

[5] Synthesis of bi-/tricyclic azasugars fused thiazinan-4-one and their HIV-RT inhibitory activity [J].

Chen, Hua ;

Hao, Le ;

Zhu, Mo ;

Yang, Tianyu ;

Wei, Sinan ;

Qin, Zhanbin ;

Zhang, Pingzhu ;

Li, Xiaoliu .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (15) :3426-3429

[6] TOTAL SYNTHESIS OF LONGIFOLENE [J].

COREY, EJ ;

OHNO, M ;

MITRA, RB ;

VATAKENCHERRY, PA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (03) :478-&

[7] Escaping from Flatland: Substituted Bridged Pyrrolidine Fragments with Inherent Three-Dimensional Character [J].

Cox, Brian ;

Zdorichenko, Victor ;

Cox, Philip B. ;

Booker-Milburn, Kevin, I ;

Paumier, Romain ;

Elliott, Luke D. ;

Robertson-Ralph, Michael ;

Bloomfield, Graham .

ACS MEDICINAL CHEMISTRY LETTERS, 2020, 11 (06) :1185-1190

[8] Escaping from Flatland: [2+2] Photocycloaddition; Conformationally Constrained sp3-rich Scaffolds for Lead Generation [J].

Cox, Brian ;

Booker-Milburn, Kevin I. ;

Elliot, Luke D. ;

Robertson-Ralph, Michael ;

Zdorichenko, Victor .

ACS MEDICINAL CHEMISTRY LETTERS, 2019, 10 (11) :1512-1517

[9] Copper-Catalyzed Dearomative trans-1,2-Carboamination [J].

Davis, Christopher W. ;

Li, Yanrong ;

Zhang, Yu ;

Siddiqi, Zohaib ;

Liu, Peng ;

Sarlah, David .

ACS CATALYSIS, 2024, 14 (13) :10132-10137

[10]

Floreancig PE., 2010, J. Am. Chem. Soc, V132, P6865, DOI [10.1021/ja103004f, DOI 10.1021/JA103004F]

← 1 2 3 4 5 →