DOI QR코드

DOI QR Code

Photochemical Approach to the Preparation of Lariat Crown Ethers Containing Peptide Sidearms

  • Cho, Dae-Won (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Quan, Chunsheng (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Park, Hea-Jung (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Yoon, Ung-Chan (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Mariano, Patrick S. (Department of Chemistry and Chemical Biology, University of New Mexico)
  • 투고 : 2010.11.01
  • 심사 : 2010.11.30
  • 발행 : 2011.02.20

초록

New types of lariat type crown ethers containing peptide sidearms were prepared by using a novel strategy employing single electron transfer (SET)-induced photocyclization reactions of $\alpha$-silylether terminated phthalimides. Reactions of chiral substrates in this series produced diastereomeric mixtures of crown ether products as a result of the formation of new stereogenic center generation in the photocyclization process.

키워드

참고문헌

  1. Gokel, G. W. Crown Ethers and Cryptands; Royal Society of Chemistry: Oxford, 1991.
  2. Gustowski, D. A.; Echegoyen, L.; Goli, D. M.; Kaifer, A.; Gokel, G. W. J. Am. Chem. Soc. 1984, 106, 1633. https://doi.org/10.1021/ja00318a014
  3. Echegoyen, L.; Delgado, M.; Gatto, V. J.; Gokel, G. W.; Echegoyen, L. J. Am. Chem. Soc. 1986, 108, 6825. https://doi.org/10.1021/ja00281a072
  4. Gokel, G. W.; Leevy, W. M.; Weber, M. E. Chem. Rev. 2004, 104, 2723. https://doi.org/10.1021/cr020080k
  5. Goli, D. M.; Dishong, D. M.; Diamond, C. J.; Gokel, G. W. Tetrahedron Lett. 1982, 23, 5243 https://doi.org/10.1016/S0040-4039(00)85809-8
  6. Dishong, D. M.; Diamond, C. J.; Cinoman, M. I.; Gokel, G. W. J. Am. Chem. Soc. 1983, 105, 586. https://doi.org/10.1021/ja00341a045
  7. Moczar, I.; Peragovics, A.; Baranyai, C.; Toth, K.; Huszthy, P. Tetrahedron 2010, 66, 2953. https://doi.org/10.1016/j.tet.2010.02.076
  8. Wang, R.; Zhao, Z.; Mariano, P. S.; Choi, K. H.; Kim, S. H.; Yoon, U. C. J. photochem. photobiol. A: Chem. 2005, 175, 232. https://doi.org/10.1016/j.jphotochem.2005.05.005
  9. Maeda, H.; Tierney, D. L.; Mariano, P. S.; Banerjee, M.; Cho, D. W.; Yoon, U. C. Tetrahedron 2008, 64, 5268. https://doi.org/10.1016/j.tet.2008.03.031
  10. de Silva, A. P.; Fox, D. B.; Huxley, A. J. M.; Moody, T. S. Coord. Chem. Rev. 2000, 205, 41. https://doi.org/10.1016/S0010-8545(00)00238-1
  11. Kimura, K.; Shono, T. Cation Binding by Macrocycles; Inoue, Y., Gokel, G. W., Eds.; Marcel Dekker: New York, 1990; p 429.
  12. Tsubaki, K.; Tanaka, H.; Kinoshita, T.; Fuji, K. Tetrahedron 2002, 58(9), 1679. https://doi.org/10.1016/S0040-4020(02)00074-1
  13. Kyba, E. P.; Siegel, M. G.; Sousa, L. R.; Sogah, G. D. Y.; Cram, D. J. J. Am. Chem. Soc. 1973, 95, 2691. https://doi.org/10.1021/ja00789a050
  14. Kyba, E. B.; Koga, K.; Sousa, L. R.; Seigel, M. G.; Cram, D. J. J. Am. Chem. Soc. 1973, 95, 2692. https://doi.org/10.1021/ja00789a051
  15. Peacock, S. C.; Domeier, L. A.;Gaeta, F. C. A.; helgeson, R. C.; Timko, J. M.; Cram, D. J. J. Am. Chem. Soc. 1978, 100, 8190. https://doi.org/10.1021/ja00494a029
  16. Ernesto, A.; Maguire, G. E. M.; Murillo, O.; Suzuki, I.; De Wall, S. L.; Gokel, G. W. J. Am. Chem. Soc. 1999, 121, 9043 https://doi.org/10.1021/ja9909172
  17. Yoon, U. C.; Oh, S. W.; Lee, C. W. Heterocycles 1995, 41(2), 2665. https://doi.org/10.3987/COM-95-7029
  18. Yoon, U. C.; Oh, S. W.; Lee, J. H.; Park, J. H.; Kang, K. T.; Mariano, P. S. J. Org. Chem. 2001, 66, 939. https://doi.org/10.1021/jo001457u
  19. Yoon, U. C.; Mariano, P. S. Acc. Chem. Res. 2001, 34, 523. https://doi.org/10.1021/ar010004o
  20. Yoon, U. C.; Jin, Y. X.; Oh, S. W.; Park, C. H.; Park, J. H.; Campana, C. F.; Cai, X.; Duesler, E. N.; Mariano, P. S. J. Am. Chem. Soc. 2003, 125, 10664. https://doi.org/10.1021/ja030297b
  21. Sung, N. K.; Cho, D. W.; Choi, J. H.; Choi, K, W.; Yoon, U. C.;Maeda, H.; Mariano, P. S. J. Org. Chem. 2007, 72, 8831. https://doi.org/10.1021/jo701770x
  22. Cho, D. W.; Quan, C.; Park, H. J.; Choi, J. H.; Kim, S. R.; Hyung, T. G.; Yoon, U. C.; Kim, S. H.; Jin, Y. X.; Mariano, P. S. Tetrahedron 2010, 66, 3173. https://doi.org/10.1016/j.tet.2010.02.074
  23. Yoon, U. C.; Kwon, H. C.; Hyung, T. G.; Choi, K. H.; Oh, S. W.; Yang, S.; Zhao, Z.; Mariano, P. S. J. Am. Chem. Soc. 2004, 126, 1110. https://doi.org/10.1021/ja0305712
  24. Cho, D. W.; Choi, J. H.; Oh, S. W.; Quan, C.; Yoon, U. C.; Wang, R.; Yang, S.; Mariano, P. S. J. Am. Chem. Soc. 2008, 130(7), 2276. https://doi.org/10.1021/ja076846l
  25. Wright, L. R.; Borkman, R. R. J. Am. Chem. Soc. 1980, 102, 6207. https://doi.org/10.1021/ja00540a006
  26. Paterson, Y.; Leach, S. J. Macromolecules 1978, 11(2), 409. https://doi.org/10.1021/ma60062a024
  27. Liebman, J. F.; Greenberg, A. Biophys. Chem. 1974, 1(3), 222. https://doi.org/10.1016/0301-4622(74)80008-6

피인용 문헌

  1. ChemInform Abstract: Photochemical Approach to the Preparation of Lariat Crown Ethers Containing Peptide Sidearms. vol.42, pp.22, 2011, https://doi.org/10.1002/chin.201122207
  2. -Glucopyranoside Based Lariat Ether Catalysts in Asymmetric Syntheses vol.26, pp.1, 2014, https://doi.org/10.1002/hc.21214
  3. Direct and indirect single electron transfer (SET)-photochemical approaches for the preparation of novel phthalimide and naphthalimide-based lariat-type crown ethers vol.10, pp.None, 2014, https://doi.org/10.3762/bjoc.10.47