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Hydroarylation for the Facile Synthesis of 2-Substituted Tetrahydroquinoline: A Concise Synthesis of (+)-(S)-Angustureine

  • Published : 2006.05.20

Abstract

Keywords

References

  1. Katritzky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031 https://doi.org/10.1016/S0040-4020(96)00911-8
  2. Jacquemond-Collet, I.; Hannedouche, S.; Fabre, N.; Fouraste, I.;Moulis, C. Phytochemistry 1999, 51, 1167 https://doi.org/10.1016/S0031-9422(99)00032-1
  3. Mester, I. Fitoterapia 1973, 44, 123
  4. Houghton, P. J.; Woldemariam, T. Z.; Watanabe, T.; Yates, M.Planta Med. 1999, 65, 250 https://doi.org/10.1055/s-1999-13988
  5. Jacquemond-Collet, I.; Benoit-Vical, F.; Mustofa; Valentin, A.;Stanislas, E.; Mallie, M.; Fouraste, I. Planta Med. 2002, 68, 68 https://doi.org/10.1055/s-2002-19869
  6. Mitsunobu, O.; Jenkins, I. D. In Encyclopedia of Reagents forOrganic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; Vol. 8, p 5379
  7. Mitsunobu, O. Synthesis 1981, 1
  8. Shi, Z.; He, C. J. Org. Chem. 2004, 69, 3669 https://doi.org/10.1021/jo0497353
  9. Nishizawa, M.; Takao, H.; Yadav, V. K.; Imagawa, H.; Sugihara,T. Org. Lett. 2003, 5, 4563 https://doi.org/10.1021/ol035622e
  10. Williamson, N. M.; Ward, D. A. Tetrahedron 2004, 61, 155 https://doi.org/10.1016/j.tet.2004.10.035
  11. Pastine, S. J.; Youn, S. W.; Sames, D. Org. Lett.2003, 5,1055 https://doi.org/10.1021/ol034177k
  12. Pastine, S. J.; Youn, S. W.; Sames, D. Tetrahedron 2003, 59, 8859 https://doi.org/10.1016/j.tet.2003.05.003
  13. Theeraladanon, C.; Arisawa, M.; Nakagawa, M.; Nishida, A. Tetrahedron: Asymmetry 2005, 16, 827 https://doi.org/10.1016/j.tetasy.2004.12.022

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  1. Advances in the Chemistry of Tetrahydroquinolines vol.111, pp.11, 2011, https://doi.org/10.1021/cr100307m
  2. )-(−)-Angustureine vol.13, pp.10, 2011, https://doi.org/10.1021/ol200625h
  3. -Aminostyrenes vol.133, pp.46, 2011, https://doi.org/10.1021/ja2092954
  4. Enantioselective Syntheses of Tetrahydroquinolines Based on Iridium-Catalyzed Allylic Substitutions: Total Syntheses of (+)-Angustureine and (-)-Cuspareine vol.2011, pp.34, 2011, https://doi.org/10.1002/ejoc.201100981
  5. Enantiospecific Synthesis of (-)-Cuspareine and (-)-Galipinine vol.52, pp.6, 2014, https://doi.org/10.1002/jhet.2112
  6. An enantioselective approach to 2-alkyl substituted tetrahydroquinolines: total synthesis of (+)-angustureine vol.5, pp.49, 2015, https://doi.org/10.1039/C5RA05987A
  7. Hydroarylation for the Facile Synthesis of 2-Substituted Tetrahydroquinoline: A Concise Synthesis of (+)-(S)-Angustureine. vol.37, pp.51, 2006, https://doi.org/10.1002/chin.200651195
  8. Efficient Synthesis of 2-Substituted 2,3-Dihydro-4-quinolones as Potential Intermediates for 2-Substituted 1,2,3,4-Tetrahydro-4-quinolone Antitumor Agents vol.29, pp.5, 2006, https://doi.org/10.1007/bf02968586
  9. Quinoline, quinazoline and acridone alkaloids vol.25, pp.1, 2006, https://doi.org/10.1039/b612168n
  10. A copper(II)-catalyzed, sequential Michael-aldol reaction for the preparation of 1,2-dihydroquinolines vol.53, pp.7, 2012, https://doi.org/10.1016/j.tetlet.2011.12.017
  11. Synthesis of 1,2,3,4-Tetrahydroquinolines including Angustureine and Congeneric Alkaloids. A Review vol.47, pp.3, 2006, https://doi.org/10.1080/00304948.2015.1025012
  12. An intramolecular C–N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis vol.11, pp.None, 2015, https://doi.org/10.3762/bjoc.11.99
  13. The Hancock Alkaloids Angustureine, Cuspareine, Galipinine, and Galipeine: A Review of their Isolation, Synthesis, and Spectroscopic Data vol.2019, pp.31, 2019, https://doi.org/10.1002/ejoc.201900493
  14. Asymmetric Total Syntheses of (−)-Angustureine and (−)-Cuspareine via Rhodium-Catalyzed Hydroamination vol.22, pp.2, 2006, https://doi.org/10.1021/acs.orglett.9b04334