Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Catalytic Asymmetric Construction of the exo-7-Aryl-6,8-dioxabicyclo[3.2.1]octane Framework of Psoracorylifols B and C Using a Carbonyl Ylide Cycloaddition Strategy

  • Published : 2010.03.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Yin, S.; Fan, C.-Q.; Dong, L.; Yue, J.-M. Tetrahedron 2006, 62,2569. https://doi.org/10.1016/j.tet.2005.12.041
  2. Matsuda, H.; Sugimoto, S.; Morikawa, T.; Matsuhira, K.; Mizuguchi,E.; Nakamura, S.; Yoshikawa, M. Chem. Pharm. Bull. 2007,55, 106. https://doi.org/10.1248/cpb.55.106
  3. Milroy, L.-G.; Zinzalla, G.; Prencipe, G.; Michel, P.; Ley, S. V.;Gunaratnam, M.; Beltran, M.; Neidle, S. Angew. Chem. Int. Ed.2007, 46, 2493 and references cited therein. https://doi.org/10.1002/anie.200604688
  4. Mundy, B. P.; Lipkowitz, K. B.; Dirks, G. W.Heterocycles 1977, 6, 51. https://doi.org/10.3987/R-1977-01-0051
  5. Mori, K. Tetrahedron 1989, 45, 3233. https://doi.org/10.1016/S0040-4020(01)81007-3
  6. Kotsuki, H. Synlett 1992, 97.
  7. Jun, J.-G. Synlett 2003, 1759.
  8. Padwa, A. Acc. Chem. Res. 1991,24, 22. https://doi.org/10.1021/ar00001a004
  9. Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. https://doi.org/10.1021/cr00003a001
  10. Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. https://doi.org/10.1016/S0040-4020(01)88298-3
  11. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. https://doi.org/10.1021/cr950022h
  12. Doyle,M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods forOrganic Synthesis with Diazo Compounds; Wiley-Interscience:New York, 1998; Chapter 7.
  13. Mehta, G.; Muthusamy, S. Tetrahedron2002, 58, 9477. https://doi.org/10.1016/S0040-4020(02)01187-0
  14. McMills, M. C.; Wright, D. In SyntheticApplications of 1,3-Dipolar Cycloaddition Chemistry TowardHeterocycles and Natural Products; Padwa, A., Pearson, W. H.,Eds.; John Wiley & Sons: Hoboken, 2003; Chapter 4.
  15. Savizky,R. M.; Austin, D. J. In Modern Rhodium-Catalyzed Organic Reactions;Evans P. A., Ed.; Wiley-VCH: Weinheim, 2005; Chapter19.
  16. Padwa, A. Helv. Chim. Acta 2005, 88, 1357. https://doi.org/10.1002/hlca.200590109
  17. Padwa, A.J. Organomet. Chem. 2005, 690, 5533. https://doi.org/10.1016/j.jorganchem.2005.06.010
  18. de March, P.; Huisgen, R. J. Am.Chem. Soc. 1982, 104, 4952. https://doi.org/10.1021/ja00382a038
  19. Padwa, A.; Fryxell, G. E.; Zhi, L.J. Org. Chem. 1988, 53, 2875. https://doi.org/10.1021/jo00247a051
  20. Padwa, A.; Chinn, R. L.; Hornbuckle,S. F.; Zhi, L. Tetrahedron Lett. 1989, 30, 301. https://doi.org/10.1016/S0040-4039(00)95185-2
  21. Padwa,A.; Chinn, R. L.; Zhi, L. Tetrahedron Lett. 1989, 30, 1491. https://doi.org/10.1016/S0040-4039(00)99499-1
  22. Padwa, A.; Fryxell, G. E.; Zhi, L. J. Am. Chem. Soc. 1990, 112,3100. https://doi.org/10.1021/ja00164a034
  23. Padwa, A.; Chinn, R. L.; Hornbuckle, S. F.; Zhang, Z. J.J. Org. Chem. 1991, 56, 3271. https://doi.org/10.1021/jo00010a019
  24. Alt, M.; Maas, G. Tetrahedron1994, 50, 7435. https://doi.org/10.1016/S0040-4020(01)90472-7
  25. Koyama, H.; Ball, R. G.; Berger, G. D. TetrahedronLett. 1994, 35, 9185. https://doi.org/10.1016/0040-4039(94)88460-9
  26. Hodgson, D. M.; Bailey, J. M.; Harrison, T. Tetrahedron Lett. 1996, 37, 4623. https://doi.org/10.1016/0040-4039(96)00893-3
  27. Drew, M. G. B.;Fengler-Veith, M.; Harwood, L. M.; Jahans, A. W. TetrahedronLett. 1997, 38, 4521. https://doi.org/10.1016/S0040-4039(97)00919-2
  28. Doyle, M. P.; Forbes, D. C.; Protopopova,M. N.; Stanley, S. A.; Vasbinder, M. M.; Xavier, K. R. J. Org.Chem. 1997, 62, 7210. https://doi.org/10.1021/jo970641l
  29. Hodgson, D. M.; Villalonga-Barber, C.Tetrahedron Lett. 2000, 41, 5597. https://doi.org/10.1016/S0040-4039(00)00873-X
  30. Hodgson, D. M.; Bailey, J.M.; Villalonga-Barber, C.; Drew, M. G. B.; Harrison, T. J. Chem.Soc., Perkin Trans. 1 2000, 3432.
  31. Jiang, B.; Zhang, X.; Luo,Z. Org. Lett. 2002, 4, 2453. https://doi.org/10.1021/ol0200854
  32. Muthusamy, S.; Babu, S. A.; Gunanathan,C.; Ganguly, B.; Suresh, E.; Dastidar, P. J. Org. Chem.2002, 67, 8019. https://doi.org/10.1021/jo0256134
  33. Lu, C.-D.; Chen, Z.-Y.; Liu, H.; Hu, W.-H.;Mi, A.-Q. Org. Lett. 2004, 6, 3071. https://doi.org/10.1021/ol0489494
  34. Russell, A. E.; Brekan, J.;Gronenberg, L.; Doyle, M. P. J. Org. Chem. 2004, 69, 5269. https://doi.org/10.1021/jo049403y
  35. Muthusamy, S.; Krishnamurthi, J.; Nethaji, M. Tetrahedron Lett.2004, 45, 6485. https://doi.org/10.1016/j.tetlet.2004.06.119
  36. Muthusamy, S.; Gnanaprakasam, B. Tetrahedron2005, 61, 1309. https://doi.org/10.1016/j.tet.2004.11.008
  37. eAngelis, A.; Panne, P.; Yap, G. P.A.; Fox, J. M. J. Org. Chem. 2008, 73, 1435. https://doi.org/10.1021/jo702308f
  38. Hodgson, D. M.; Pierard, F. Y. T. M.; Stupple,P. A. Chem. Soc. Rev. 2001, 30, 50. https://doi.org/10.1039/b000708k
  39. Hodgson, D. M.; Stupple,P. A.; Johnstone, C. Tetrahedron Lett. 1997, 38, 6471. https://doi.org/10.1016/S0040-4039(97)01480-9
  40. Hodgson,D. M.; Stupple, P. A.; Johnstone, C. Chem. Commun. 1999, 2185.
  41. Hodgson, D. M.; Stupple, P. A.; Pierard, F. Y. T. M.; Labande,A. H.; Johnstone, C. Chem. Eur. J. 2001, 7, 4465. https://doi.org/10.1002/1521-3765(20011015)7:20<4465::AID-CHEM4465>3.0.CO;2-W
  42. Hodgson, D.M.; Brückl, T.; Glen, R.; Labande, A. H.; Selden, D. A.; Dossetter,A. G.; Redgrave, A. J. Proc. Natl. Acad. Sci. U. S. A. 2004, 101,5450. https://doi.org/10.1073/pnas.0307274101
  43. Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911. https://doi.org/10.1021/cr940066a
  44. Kitagaki, S.; Anada, M.; Kataoka, O.;Matsuno, K.; Umeda, C.; Watanabe, N.; Hashimoto, S. J. Am.Chem. Soc. 1999, 121, 1417. https://doi.org/10.1021/ja983748e
  45. Kitagaki, S.; Yasugahira, M.;Anada, M.; Nakajima, M.; Hashimoto, S. Tetrahedron Lett. 2000,41, 5931. https://doi.org/10.1016/S0040-4039(00)00977-1
  46. Shimada, N.; Anada, M.; Nakamura, S.; Nambu, H.;Tsutsui, H.; Hashimoto, S. Org. Lett. 2008, 10, 3603. https://doi.org/10.1021/ol8013733
  47. Suga, H.; Inoue, K.; Inoue, S.; Kakehi, A. J. Am.Chem. Soc. 2002, 124, 14836. https://doi.org/10.1021/ja028676c
  48. Suga, H.; Inoue, K.; Inoue, S.;Kakehi, A.; Shiro, M. J. Org. Chem. 2005, 70, 47. https://doi.org/10.1021/jo049007f
  49. Suga, H.;Ishimoto, D.; Higuchi, S.; Ohtsuka, M.; Arikawa, T.; Tsuchida,T.; Kakehi, A.; Baba, T. Org. Lett. 2007, 9, 4359. https://doi.org/10.1021/ol701936b
  50. Tsutsui, H.; Shimada, N.; Abe, T.; Anada, M.; Nakajima, M.;Nakamura, S.; Nambu, H.; Hashimoto, S. Adv. Synth. Catal. 2007,349, 521. https://doi.org/10.1002/adsc.200600591

Cited by

  1. Recent Developments in the [5+2] Cycloaddition vol.353, pp.2-3, 2011, https://doi.org/10.1002/adsc.201000695
  2. Recent Developments in Enantioselective Metal-Catalyzed Domino Reactions vol.354, pp.18, 2012, https://doi.org/10.1002/adsc.201200254
  3. -Psoracorylifol C vol.16, pp.11, 2014, https://doi.org/10.1021/ol501120m
  4. Recent Advances of Catalytic Asymmetric 1,3-Dipolar Cycloadditions vol.115, pp.11, 2015, https://doi.org/10.1021/cr5007182
  5. Modern Organic Synthesis with α-Diazocarbonyl Compounds vol.115, pp.18, 2015, https://doi.org/10.1021/acs.chemrev.5b00121
  6. Chiral Lewis Acid-Catalyzed Enantioselective Cycloadditions between Indoles and Cyclic Carbonyl Ylides Derived from Diazodiketone or Diazoketoester Derivatives vol.80, pp.13, 2015, https://doi.org/10.1021/acs.joc.5b00835
  7. Synthetic Approaches To Construct the 6,8-DOBCO Framework in Natural Products vol.81, pp.6, 2016, https://doi.org/10.1021/acs.joc.6b00246
  8. Recent Developments in the [5+2] Cycloaddition vol.360, pp.8, 2018, https://doi.org/10.1002/adsc.201701379
  9. asymmetric 1,3-dipolar cycloadditions of cyclic azomethine ylides using a dual catalytic system vol.55, pp.11, 2019, https://doi.org/10.1039/C8CC09224A
  10. ChemInform Abstract: Catalytic Asymmetric Construction of the exo-7-Aryl-6,8-dioxabicyclo[3.2.1]octane Framework of Psoracorylifols B and C Using a Carbonyl Ylide Cycloaddition Strategy. vol.41, pp.32, 2010, https://doi.org/10.1002/chin.201032206
  11. Diastereoselective Access to Polyoxygenated Polycyclic Spirolactones through a Rhodium‐Catalyzed [3+2] Cycloaddition Reaction: Experimental and Theoretical Studies vol.19, pp.7, 2010, https://doi.org/10.1002/chem.201203155
  12. Synthetic Approach to the Psoracorylifols vol.9, pp.3, 2010, https://doi.org/10.1177/1934578x1400900305
  13. Catalytic Asymmetric 1,3-Dipolar Cycloaddition Reactions Based on Ylide Formation Reactions vol.77, pp.10, 2010, https://doi.org/10.5059/yukigoseikyokaishi.77.1014