1,3-Dipolar cycloaddition reaction of a D-galactose derived nitrone with allyl alcohol: synthesis of polyhydroxylated perhydroazaazulene alkaloids

被引：14
|
作者：
Bande, Omprakash P.
Jadhav, Vrushali H.
Puranik, Vedavati G.
Dhavale, Dilip D. [1 ]
机构：
[1] Univ Poona, Garware Res Ctr, Dept Chem, Pune 411007, Maharashtra, India
[2] Natl Chem Lab, Ctr Mat Characterizat, Pune 411008, Maharashtra, India
来源：
TETRAHEDRON-ASYMMETRY | 2007年 / 18卷 / 10期
关键词：
D O I：
10.1016/j.tetasy.2007.05.012
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Diastereofacial intermolecular 1,3-dipolar cycloaddition of D-galactose derived nitrone with allyl alcohol followed by tosylation afforded, in a 1:1 ratio endo- and exo-isooxazolidines 4a and 4b with complete diastereoselectivity at the nitrone carbon. The N-O bond reductive cleavage and S(N)2 displacement afforded the pyrrolidine ring with a galactose appendage that on acetonide cleavage and reductive amino-cyclization afforded pentahydroxylated perhydroazaazulenes 1a and 1b. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1176 / 1182
页数：7
相关论文
共 50 条
  • [21] Synthesis and Characterization of Isoxazolidine Derivatives by 1,3-Dipolar Cycloaddition Reaction
    Al-Ghorbani, Mohammad
    Al-Timari, Usama S.
    Fadh, Taha A.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 29 (02) : 131 - 137
  • [22] Visible-Light-Mediated Anti-Regioselective Nitrone 1,3-Dipolar Cycloaddition Reaction and Synthesis of Bisindolylmethanes
    Zheng, Lewei
    Gao, Fei
    Yang, Chao
    Gao, Guo-Lin
    Zhao, Yating
    Gao, Yuan
    Xia, Wujiong
    ORGANIC LETTERS, 2017, 19 (19) : 5086 - 5089
  • [23] Synthesis and 1,3-dipolar cycloaddition reaction of N-phenyl chloral nitrone with N-substituted maleimides
    Chakraborty, B
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 7 (01) : 77 - 78
  • [24] The 1,3-dipolar cycloaddition reaction of chiral carbohydrate-derived nitrone and olefin: towards long-chain sugars
    Oukani, Hassan
    Pellegrini-Moise, Nadia
    Jackowski, Olivier
    Chretien, Francoise
    Chapleur, Yves
    CARBOHYDRATE RESEARCH, 2013, 381 : 205 - 214
  • [25] Intramolecular 1,3-dipolar nitrone cycloaddition route to bicyclic fused enediyne
    Basak, A
    Ghosh, SC
    TETRAHEDRON LETTERS, 2005, 46 (43) : 7385 - 7388
  • [26] Microwave assisted one pot 1,3-dipolar cycloaddition reactions of novel dihydropyran derived nitrone
    Chakraborty, Bhaskar
    Sharma, Prawin Kumar
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2012, 89 (06) : 841 - 847
  • [27] Diastereoselectivity of nitrone 1,3-dipolar cycloaddition to Baylis-Hillman adducts
    Dugovic, B
    Fisera, L
    Hametner, C
    Prónayová, N
    ARKIVOC, 2003, : 162 - 169
  • [28] Functionalized azabicycloalkane amino acids by nitrone 1,3-dipolar intramolecular cycloaddition
    Manzoni, L
    Arosio, D
    Belvisi, L
    Bracci, A
    Colombo, M
    Invernizzi, D
    Scolastico, C
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10): : 4124 - 4132
  • [29] The Huisgen Reaction: Milestones of the 1,3-Dipolar Cycloaddition
    Breugst, Martin
    Reissig, Hans-Ulrich
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (30) : 12293 - 12307
  • [30] The Reactivity of Addends in the 1,3-Dipolar Cycloaddition Reaction
    Samuilovand, Ya.D.
    Konovalov, A.I.
    Russian Chemical Reviews, 1984, 53 (04) : 332 - 342
12345