Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of Calycotomine via Pictet-Spengler Type Reaction of N,O-Acetal TMS Ethers as N-Acyliminium Ion Equivalents

  • Yang, Jung-Eun (College of Pharmacy, Chungbuk National University) ;
  • In, Jin-Kyung (College of Pharmacy, Chungbuk National University) ;
  • Lee, Mi-Sung (College of Pharmacy, Chungbuk National University) ;
  • Kwak, Jae-Hwan (College of Pharmacy, Chungbuk National University) ;
  • Lee, Hee-Soon (College of Pharmacy, Chungbuk National University) ;
  • Lee, Soo-Jae (College of Pharmacy, Chungbuk National University) ;
  • Kang, Han-Young (Department of Chemistry, Institute for Basic Science, Chungbuk National University) ;
  • Suh, Young-Ger (College of Pharmacy, Seoul National University) ;
  • Jung, Jae-Kyung (College of Pharmacy, Chungbuk National University)
  • Published : 2007.08.20
Download PDF
⟨ Previous Next ⟩

Abstract

An efficient Pictet-Spengler type reaction of N,O-acetal TMS ethers for the practical synthesis of 1-substituted tetrahydroquinolines, medicinally important alkaloids, has been accomplished. To demonstrate the versatility of this novel procedure, the total synthesis of calycotomine, a representative 1-hydroxymethyl substituted tetrahydroisoquinoline, is also described.

Keywords

References

  1. Bentley, K. W. The Isoquinoline Alkaloids Harwood Academic Publishers: Amsterdam, The Netherlands, 1998
  2. Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1668
  3. Kleeman, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substances, 4th Ed.; Thieme: New York, 2001
  4. Naylor, P.; Bradshaw, J.; Bays, D. E.; Hayes, A. G.; Judd, D. B. Eur. Pat. Appl. 1989, 18
  5. Nagatsu, T. Neurosci. Res. 1997, 29, 99 https://doi.org/10.1016/S0168-0102(97)00083-7
  6. Yamakawa, T.; Ohta, S. Biochem. Biophys. Res. Commun. 1997, 236, 676 https://doi.org/10.1006/bbrc.1997.6946
  7. Kase, H.; Fujita, H.; Nakamura, J.; Hashizume, K.; Goto, J.; Kubo, K.; Shutto, K. J. Antibiot. 1986, 39, 354 https://doi.org/10.7164/antibiotics.39.354
  8. Guerry, P.; Stalder, H.; Wyss, P. C. PCT Int. Appl. 1997, 65
  9. Kaufman, T. S. Synthesis 2005, 339
  10. Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 3341 https://doi.org/10.1021/cr030692k
  11. Suh, Y.-G.; Kim, S.-H.; Jung, J.-K.; Shin, D.-Y. Tetrahedron Lett. 2002, 43, 3165
  12. Suh, Y.-G.; Shin, D.-Y.; Jung, J.-K.; Kim, S.-H. Chem. Commum. 2002, 1064
  13. Shin, D.-Y.; Jung, J.-K.; Seo, S.-Y.; Lee, Y.-S.; Paek, S.-M.; Chung, Y. K.; Shin, D. M.; Suh, Y.-G. Org. Lett. 2003, 5, 3635 https://doi.org/10.1021/ol035289e
  14. Jung, J.-W.; Shin, D.-Y.; Seo, S.-Y.; Kim, S.-H.; Paek, S.-M.; Jung, J.-K.; Suh, Y.-G.. Tetrahedron Lett. 2005, 46, 573 https://doi.org/10.1016/j.tetlet.2004.11.136
  15. Kanemitsu, T.; Yamashita, Y.; Nagata, K.; Itoh, T. Synlett 2006, 1595
  16. Pedrosa, R.; Andres, C.; Iglesias, J. M. J. Org. Chem. 2001, 66, 243 https://doi.org/10.1021/jo001397s
  17. Czarnocki, Z.; Ziolkowski, M.; Leniewski, A.; Maurin, J. K. Enantiomer 1997, 4, 71
  18. Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry 1998, 9, 183 https://doi.org/10.1016/S0957-4166(97)00635-6

Cited by

  1. Inhibition of dipeptidyl peptidase IV (DPP IV) is one of the mechanisms explaining the hypoglycemic effect of berberine vol.24, pp.5, 2009, https://doi.org/10.1080/14756360802610761
  2. One-pot reductive coupling of N-acylcarbamates with activated alkenes: application to the asymmetric synthesis of pyrrolo[1,2-a]azepin-5-one ring system and (−)-xenovenine vol.10, pp.6, 2012, https://doi.org/10.1039/C1OB06697H
  3. -Acyliminium Ions vol.117, pp.12, 2017, https://doi.org/10.1021/acs.chemrev.6b00806
  4. ChemInform Abstract: Synthesis of Calycotomine (VI) via Pictet-Spengler Type Reaction of N,O-Acetal TMS Ethers as N-Acyliminium Ion Equivalents. vol.39, pp.2, 2008, https://doi.org/10.1002/chin.200802198
  5. Preparation of Boronated Heterocyclic Compounds Using Intramolecular Cyclization Reaction vol.29, pp.2, 2007, https://doi.org/10.5012/bkcs.2008.29.2.357
  6. Synthesis of Calycotomine and N-Methylcalycotomine Using a Petasis Reaction - Pomeranz-Fritsch-Bobbitt Cyclization Sequence vol.86, pp.2, 2007, https://doi.org/10.3987/com-12-s(n)59