Spiroisoxazoline synthesis via intramolecular cyclization/methylation

被引:9
作者
Xu, Jianping [1 ]
Wang, Jun [1 ]
Ellis, Erick D. [1 ]
Hamme, Ashton T., II [1 ]
机构
[1] Jackson State Univ, Dept Chem, Jackson, MS 39217 USA
来源
SYNTHESIS-STUTTGART | 2006年 / 22卷 / 22期
关键词
spiro compounds; regioselectivity; cycloadditions; ring closure; heterocycles;
D O I
10.1055/s-2006-950302
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of regioisomeric spiroisoxazolines was achieved through an intramolecular cyclization/methylation reaction of a functionalized 5,5 -disubstituted isoxazoline in one reaction vessel. The 5,5-isoxazoline was constructed through a 1,3-dipolar cycloaddition reaction of an aromatic nitrile oxide and a geminal disubstituted alkene.
引用
收藏
页码:3815 / 3818
页数:4
相关论文
共 32 条
  • [1] Multicomponent synthesis of spiroisoxazolines
    Adamo, MFA
    Donati, D
    Duffy, EF
    Sarti-Fantoni, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21) : 8395 - 8399
  • [2] The reactivity of 3-methyl-4-nitro-5-styrylisoxazole with some bis-enolisable ketones
    Adamo, MFA
    Chimichi, S
    De Sio, F
    Donati, D
    Sarti-Fantoni, P
    [J]. TETRAHEDRON LETTERS, 2002, 43 (23) : 4157 - 4160
  • [3] Total synthesis and stereochemical assignment of the spiroisoxazoline natural product (+)-calafianin
    Bardhan, S
    Schmitt, DC
    Porco, JA
    [J]. ORGANIC LETTERS, 2006, 8 (05) : 927 - 930
  • [4] Approaches to the synthesis of some tyrosine-derived marine sponge metabolites: Synthesis of verongamine and purealidin N
    Boehlow, TR
    Harburn, JJ
    Spilling, CD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (09) : 3111 - 3118
  • [5] Boers RB, 2002, EUR J ORG CHEM, V2002, P189, DOI 10.1002/1099-0690(20021)2002:1<189::AID-EJOC189>3.0.CO
  • [6] 2-8
  • [7] A HIGHLY STEREOSELECTIVE SYNTHESIS OF TRANS-TRISUBSTITUTED OLEFINIC BONDS
    BRADY, SF
    ILTON, MA
    JOHNSON, WS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (11) : 2882 - +
  • [8] 11-deoxyfistularin-3, a new cytotoxic metabolite from the caribbean sponge Aplysina fistularis insularis
    Compagnone, RS
    Avila, R
    Suárez, AI
    Abrams, OV
    Rangel, HR
    Arvelo, F
    Piña, IC
    Merentes, E
    [J]. JOURNAL OF NATURAL PRODUCTS, 1999, 62 (10): : 1443 - 1444
  • [9] Marine natural products as antituberculosis agents
    El Sayed, KA
    Bartyzel, P
    Shen, XY
    Perry, TL
    Kjawiony, JK
    Hamann, MT
    [J]. TETRAHEDRON, 2000, 56 (07) : 949 - 953
  • [10] Aerothionin, a bromotyrosine derivative with antimycobacterial activity from the marine sponge Aplysina gerardogreeni (Demospongia)
    Encarnación-Dimayuga, R
    Ramírez, MR
    Luna-Herrera, J
    [J]. PHARMACEUTICAL BIOLOGY, 2003, 41 (05) : 384 - 387