Cycloaddition reactions for the synthesis of piperidine and indolizidine alkaloids

被引：31
|
作者：
Holmes, AB
Bourdin, B
Collins, I
Davison, EC
Rudge, AJ
Stork, TC
Warner, JA
机构：
[1] University Chemical Laboratory, Cambridge CB2 1EW, Lensfield Road
来源：
PURE AND APPLIED CHEMISTRY | 1997年 / 69卷 / 03期
基金：
英国工程与自然科学研究理事会;
关键词：
D O I：
10.1351/pac199769030531
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The intramolecular nitrone dipolar cycloaddition of N-alkenylnitrone has been utilised in approaches to the synthesis of a family of indolizidines such as castanospermine and a tethered swainsonine analogue. Examples of a tandem hydroxylamino-alkyne cyclisation/dipolar trapping experiment in the synthesis of (+/-)-adaline and (+/-)-euphococcinine are outlined.
引用
收藏
页码：531 / 536
页数：6
相关论文
共 50 条
  • [1] AN ACYLNITROSO CYCLOADDITION APPROACH TO THE SYNTHESIS OF HIGHLY OXYGENATED INDOLIZIDINE ALKALOIDS
    KECK, GE
    ROMER, DR
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22): : 6083 - 6089
  • [2] An expedient total synthesis of optically active piperidine and indolizidine alkaloids (-)-β-conhydrine and (-)-lentiginosine
    Kamal, Ahmed
    Vangala, Saidi Reddy
    TETRAHEDRON, 2011, 67 (06) : 1341 - 1347
  • [3] Stereocontrolled Cyclic Nitrone Cycloaddition Strategy for the Synthesis of Pyrrolizidine and Indolizidine Alkaloids
    Brandi, Alberto
    Cardona, Francesca
    Cicchi, Stefano
    Cordero, Franca M.
    Goti, Andrea
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (32) : 7808 - 7821
  • [4] Efficient stereoselective syntheses of piperidine, pyrrolidine, and indolizidine alkaloids
    Enders, D
    Thiebes, C
    PURE AND APPLIED CHEMISTRY, 2001, 73 (03) : 573 - 578
  • [5] A Concise and Diastereoselective Synthesis of Piperidine and Indolizidine Alkaloids via Aza-Prins Cyclization
    Reddy, Basi V. Subba
    Chaya, Dudhmal N.
    Yadav, Jhillu S.
    Gree, Rene
    SYNTHESIS-STUTTGART, 2012, 44 (02): : 297 - 303
  • [6] Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived δ-lactam
    Amat, M
    Llor, N
    Hidalgo, J
    Escolano, C
    Bosch, J
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05): : 1919 - 1928
  • [7] EXTENSION OF A NUPHAR PIPERIDINE SYNTHESIS TO QUINOLIZIDINES AND AN INDOLIZIDINE
    LALONDE, RT
    MUHAMMAD, N
    WONG, CF
    STURIALE, ER
    JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (18): : 3664 - 3671
  • [8] Stereoselective Mannich Reactions in the Synthesis of Enantiopure Piperidine Alkaloids and Derivatives
    van Rootselaar, Stefan
    Peterse, Evert
    Blanco-Ania, Daniel
    Rutjes, Floris P. J. T.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (22)
  • [9] SYNTHESIS OF INDOLIZIDINE AND PYRROLIZIDINE ALKALOIDS BY THE [2+2]-CYCLOADDITION OF ENDOCYCLIC ENECARBAMATES TO ALKYL KETENES
    CORREIA, CRD
    DEFARIA, AR
    CARVALHO, ES
    TETRAHEDRON LETTERS, 1995, 36 (29) : 5109 - 5112
  • [10] Enaminones as intermediates in the synthesis of indolizidine alkaloids
    Michael, JP
    Gravestock, D
    PURE AND APPLIED CHEMISTRY, 1997, 69 (03) : 583 - 588
12345