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Pure Appl. Chem., 1997, Vol. 69, No. 3, pp. 531-536

Cycloaddition reactions for the synthesis of piperidine and indolizidine alkaloids

A. B. Holmes, B. Bourdin, Ian Collins, E. C. Davison, A. J. Rudge, T. C. Stork and J. A. Warner

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  • Thorat Rakesh G., Pansare Sunil V.: A General Approach to 1-Hydroxymethylquinolizidine and 8-Hydroxymethylindolizidine Stereoisomers: Synthesis of (+)-Epitashiromine and Formal Syntheses of (+)-Epilupinine and (+)-Tashiromine. Eur. J. Org. Chem. 2013, 2013, 7282. <>
  • Merino Pedro, Greco Graziella, Tejero Tomás, Hurtado-Guerrero Ramon, Matute Rosa, Chiacchio Ugo, Corsaro Antonino, Pistarà Venerando, Romeo Roberto: Stereoselective 1,3-dipolar cycloadditions of nitrones derived from amino acids. Asymmetric synthesis of N-(alkoxycarbonylmethyl)-3-hydroxypyrrolidin-2-ones. Tetrahedron 2013, 69, 9381. <>
  • Śnieżek Marcin, Stecko Sebastian, Panfil Irma, Furman Bartłomiej, Urbańczyk-Lipkowska Zofia, Chmielewski Marek: Thermal and Sc(OTf)3 catalyzed 1,3-dipolar cycloaddition of open-chain nitrones to α,β-unsaturated lactones: combined experimental and computational studies. Tetrahedron: Asymmetry 2013, 24, 89. <>
  • Krenske Elizabeth H., Davison Edwin C., Forbes Ian T., Warner Jacqueline A., Smith Adrian L., Holmes Andrew B., Houk K. N.: Reverse Cope Elimination of Hydroxylamines and Alkenes or Alkynes: Theoretical Investigation of Tether Length and Substituent Effects. S J Am Chem Soc 2012, 134, 2434. <>
  • Krenske Elizabeth H., Agopcan Sesil, Aviyente Viktorya, Houk K. N., Johnson Brian A., Holmes Andrew B.: Causation in a Cascade: The Origins of Selectivities in Intramolecular Nitrone Cycloadditions. J. Am. Chem. Soc. 2012, 134, 12010. <>
  • Saha Nemai, Chattopadhyay Shital K: Enantiodivergency and Enantioconvergency in the Synthesis of the Dendrobate Alkaloid 241D. J. Org. Chem. 2012, 77, 11056. <>
  • Hodges Alastair J., Adams Joseph P., Bond Andrew D., Holmes Andrew B., Press Neil J., Roughley Stephen D., Ryan John H., Saubern Simon, Smith Catherine J., Turnbull Michael D., Newton Annabella F.: Intramolecular nitrone dipolar cycloadditions: control of regioselectivity and synthesis of naturally-occurring spirocyclic alkaloids. Org. Biomol. Chem. 2012, 10, 8963. <>
  • Krenske Elizabeth H., Houk K.N., Holmes Andrew B., Thompson John: Entropy versus tether strain effects on rates of intramolecular 1,3-dipolar cycloadditions of N-alkenylnitrones. Tetrahetron Lett 2011, 52, 2181. <>
  • Coombs Thomas C., Zhang Yongqiang, Garnier-Amblard Ethel C., Liebeskind Lanny S.: Organometallic Enantiomeric Scaffolding. Sequential Semipinacol/1,5-“Michael-like” Reactions as a Strategic Approach to Bridgehead-Quaternary Center Aza[3.3.1]Bicyclics: Application to the Total Synthesis of (−)-Adaline. J Am Chem Soc 2009, 131, 876. <>
  • Merino Pedro, Tejero Tomas, Chiacchio Ugo, Romeo Giovanni, Rescifina Antonio: A DFT study on the 1,3-dipolar cycloaddition reactions of C-(hetaryl) nitrones with methyl acrylate and vinyl acetate. Tetrahedron 2007, 63, 1448. <>
  • Socha Dariusz, Paśniczek Konrad, Jurczak Margarita, Solecka Jolanta, Chmielewski Marek: Synthesis of 1-homoaustraline. Carbohydrate Research 2006, 341, 2005. <>
  • Stecko Sebastian, Paśniczek Konrad, Jurczak Margarita, Urbańczyk-Lipkowska Zofia, Chmielewski Marek: Double asymmetric induction in 1,3-dipolar cycloaddition of five-membered cyclic nitrones to 2-(5H)-furanones. Tet Asymm 2006, 17, 68. <>
  • Cossy Janine: Selective methodologies for the synthesis of biologically active piperidinic compounds. Chem Record 2005, 5, 70. <>
  • Pearson William H, Hembre Erik J: Synthesis and mannosidase inhibitory activity of 6- and 7-substituted analogs of swainsonine. Tetrahetron Lett 2001, 42, 8273. <>
  • Black David StC., Craig Donald C., Edwards Gavin L., Laaman Sean M.: Intramolecular cycloaddition of 5-alkenyl-1-pyrroline 1-oxide-5-carboxylic esters. Tetrahetron Lett 1998, 39, 5849. <>
  • P. Michael Joseph: Indolizidine and quinolizidine alkaloids. Nat Prod Rep 1998, 15, 571. <>