A sort synthesis of polyhydroxylated pyrrolizidines via sequential 1,3-dipolar cycloaddition and reductive amination

被引：10
|
作者：
Gkizis, Petros [1 ]
Argyropoulos, Nikolaos G. [1 ]
Coutouli-Argyropoulou, Evdoxia [1 ]
机构：
[1] Aristotle Univ Thessaloniki, Dept Chem, Organ Chem Lab, Thessaloniki 54124, Greece
来源：
TETRAHEDRON | 2013年 / 69卷 / 42期
关键词：
Pyrrolizidines; Reductive amination; 1,3-Dipolar cycloaddition; Nitrones; Azasugars; 1ST ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ENANTIOSPECIFIC SYNTHESIS; CYCLIC NITRONES; GLYCOSIDASE INHIBITORS; HYACINTHACINE A(1); NATURAL OCCURRENCE; ALKALOIDS; AUSTRALINE; STRATEGY;
D O I：
10.1016/j.tet.2013.07.098
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Polyhydroxylated pyrrolizidines bearing a methyl group at C-5 have been synthesized by 1,3-dipolar cycloaddition of five membered cyclic nitrones with methyl vinyl ketone followed by a N-O reductive cleavage and in situ intramolecular reductive amination. The stereochemistry of the obtained compounds is examined in relation to the reactions mechanism. (c) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8921 / 8928
页数：8
相关论文
共 50 条
  • [1] Multicomponent synthesis of unnatural pyrrolizidines using 1,3-dipolar cycloaddition of proline esters
    Mancebo-Aracil, Juan
    Najera, Carmen
    Sansano, Jose M.
    CHEMICAL COMMUNICATIONS, 2013, 49 (95) : 11218 - 11220
  • [2] Synthesis of pyrrolizidines and indolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides
    Najera, Carmen
    Miguel Sansano, Jose
    PURE AND APPLIED CHEMISTRY, 2019, 91 (04) : 575 - 596
  • [3] 1,3-dipolar cycloaddition reactions of imines of γ- and δ-dialdehydes:: Applications to the synthesis of novel polyfunctional pyrrolizidines and indolizidines
    Grigg, R
    Hargreves, S
    Redpath, J
    Turchi, S
    Yoganathan, G
    SYNTHESIS-STUTTGART, 1999, (03): : 441 - 446
  • [4] Synthesis of pyrazolines via 1,3-dipolar cycloaddition reactions
    Singh, Himanshu
    Kumar, Rajnish
    Mazumder, Avijit
    SYNTHETIC COMMUNICATIONS, 2023, 53 (11) : 755 - 770
  • [5] Practical Synthesis of Valbenazine via 1,3-Dipolar Cycloaddition
    Peng, Yalan
    Lin, Zuming
    Zhu, Lili
    Han, Shiqing
    Huang, Sha-Hua
    Hong, Ran
    CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (08) : 841 - 845
  • [6] Convenient synthesis of ferrocenyl β-C-glycosydic spiropyrrolidines and pyrrolizidines through 1,3-dipolar cycloaddition reaction
    Prasanna, R.
    Purushothaman, S.
    Suresh, M.
    Raghunathan, R.
    TETRAHEDRON LETTERS, 2011, 52 (07) : 792 - 797
  • [7] Highly Enantioselective Intramolecular 1,3-Dipolar Cycloaddition: A Route to Piperidino-Pyrrolizidines
    Vidadala, Srinivasa Rao
    Golz, Christopher
    Strohmann, Carsten
    Daniliuc, Constantin-G.
    Waldmann, Herbert
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (02) : 651 - 655
  • [8] Regio and diastereoselective multicomponent 1,3-dipolar cycloadditions between prolinate hydrochlorides, aldehydes and dipolarophiles for the direct synthesis of pyrrolizidines
    Mancebo-Aracil, Juan
    Najera, Carmen
    Castello, Luis M.
    Sansano, Jose M.
    Larranaga, Olatz
    de Cozar, Abel
    Cossio, Fernando P.
    TETRAHEDRON, 2015, 71 (52) : 9645 - 9661
  • [9] Synthesis of novel isoxazolidines via 1,3-dipolar cycloaddition of nitrones to olefins
    Kumar, BKV
    Mantelingu, K
    Basappa
    Rangappa, KS
    HETEROCYCLIC COMMUNICATIONS, 2003, 9 (02) : 161 - 164
  • [10] Synthesis of Novel Spiro Indolizidine Derivatives via 1,3-Dipolar Cycloaddition of Azomethine Ylide
    Li, Xiaofang
    Yi, Rongqiong
    Liu, Bin
    Li, Zhikui
    Yu, Xianyong
    Yi, Pinggui
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (12) : 2309 - 2314
12345