Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of Dihydropyran Subunit of (+)-Sorangicin A Using RCM Reaction

  • Park, Su-Ho (Department of Chemistry, Chungbuk National University) ;
  • Lee, Hyo-Won (Department of Chemistry, Chungbuk National University)
  • Published : 2008.09.30
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Jansen, R.; Wray, V.; Irschik, H.; Reichenbach, H.; Hofle, G. Tetrahedron Lett. 1985, 26, 6031-6034 https://doi.org/10.1016/S0040-4039(00)95117-7
  2. Jansen, R.; Irschik, H.; Reichenbach, H.; Schomburg, H.; Wray, V.; Hofle, G. Liebigs Ann. Chem. 1989, 111-119
  3. Jansen, R.; Schummer, D.; Irschik, H.; Hofle, G. Liebigs Ann. Chem. 1990, 975-988
  4. Schummer, D.; Irschik, H.; Hofle, G. Liebigs Ann. Chem. 1993, 293-304
  5. Jansen, R.; Irschik, H.; Reichenbach, H.; Wray, V.; Hofle, G. Liebigs Ann. Chem. 1989, 213-222
  6. Smith, A. B., III; Fox, R. J. Org. Lett. 2004, 6, 1477-1480 https://doi.org/10.1021/ol049644s
  7. Smith, A. B., III; Fox, R. J.; Vanecko, J. A. Org. Lett. 2005, 7, 3099-3102 https://doi.org/10.1021/ol051119l
  8. Schinzer, D.; Schulz, C.; Krug, O. Synlett 2004, 15, 2689-2692
  9. Crimmins, M. T.; Haley, M. W. Org. Lett. 2006, 8, 4223-4225 https://doi.org/10.1021/ol061339e
  10. Burke, S. D.; Armistead, D. M.; Schoenen, F. J. J. Org. Chem. 1984, 49, 4320-4322 https://doi.org/10.1021/jo00196a049
  11. Kim, S.; Fuchs, P. L. J. Am. Chem. Soc. 1991, 113, 9864-9865 https://doi.org/10.1021/ja00026a030
  12. Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659-4676 https://doi.org/10.1016/S0040-4020(01)81240-0
  13. Danishefsky, S. J.; Selnick, H. G.; Zelle, R. E.; DeNinno, M. P. J. Am. Chem. Soc. 1988, 110, 4368-4378 https://doi.org/10.1021/ja00221a043
  14. Lee, H. W.; Jeong, C. S.; Yoon, S. H.; Lee, I.-Y. C. Bull. Korean Chem. Soc. 2001, 22, 791-792
  15. Lee, H. W.; Yoon, S. H.; Lee, I.-Y. C.; Chung, B. Y. Bull. Korean Chem. Soc. 2001, 22, 1179-1180
  16. Lee, H. W.; Hong, J.-Y. Bull. Korean Chem. Soc. 2003, 24, 1569-1570 https://doi.org/10.5012/bkcs.2003.24.11.1569
  17. Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452 https://doi.org/10.1021/ar00059a002
  18. Kim, A.; Hong, J. H. Bull. Korean Chem. Soc. 2006, 27, 976-980 https://doi.org/10.5012/bkcs.2006.27.7.976
  19. Hong, Y. D.; Lee, H. W.; Lee, I. Y.-C.; Jung, J.-K. Bull. Korean Chem. Soc. 2007, 28, 367-368 https://doi.org/10.5012/bkcs.2007.28.3.367
  20. Crimmins, M. T.; She, J. Synlett 2004, 8, 1371-1374
  21. Evans, P. A.; Leahy, D. K.; Andrews, W. J.; Uraguchi, D. Angew. Chem., Int. Ed. Engl. 2004, 43, 4788-4791 https://doi.org/10.1002/anie.200460612
  22. Evans, P. A.; Nelson, J. D. J. Am. Chem. Soc. 1998, 120, 5581- 5582 https://doi.org/10.1021/ja980030q

Cited by

  1. Total Synthesis of (+)-Sorangicin A vol.131, pp.34, 2009, https://doi.org/10.1021/ja906115a
  2. An Asymmetric Tandem Conjugative Addition-Intramolecular Cyclisation Process to Provide Functionalised 3,6-Dihydropyrans and 4,5-Epoxytetrahydropyrans vol.2010, pp.1, 2009, https://doi.org/10.1002/ejoc.200901145
  3. Formal Synthesis of (+)-Sorangicin A vol.13, pp.17, 2011, https://doi.org/10.1021/ol201920j
  4. Stereoselective Synthesis of Tetrahydropyrans through Tandem and Organocatalytic Oxa-Michael Reactions: Synthesis of the Tetrahydropyran Cores of ent-(+)-Sorangicin A vol.2012, pp.5, 2011, https://doi.org/10.1002/ejoc.201101549
  5. A stereoselective approach for the southeast segment (C1–C16) of (+)-sorangicin A vol.11, pp.28, 2013, https://doi.org/10.1039/c3ob40985f
  6. ChemInform Abstract: Synthesis of Dihydropyran Subunit of (+)-Sorangicin A Using RCM Reaction. vol.40, pp.6, 2009, https://doi.org/10.1002/chin.200906210
  7. A carbohydrate approach for the synthesis of tetrahydropyran containing C16–C29 fragment of sorangicin A vol.65, pp.32, 2008, https://doi.org/10.1016/j.tet.2009.06.035
  8. The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2008 vol.254, pp.1, 2008, https://doi.org/10.1016/j.ccr.2009.07.018
  9. Iodine-Catalyzed Highly Diastereoselective Synthesis of trans-2,6-Disubstituted-3,4-Dihydropyrans: Application to Concise Construction of C28–C37 Bicyclic Core of (+)-Sorangicin A vol.16, pp.7, 2008, https://doi.org/10.1002/chem.200902999
  10. Convergent Stereoselective Synthesis of the C16-C37 Subunit of Sorangicin A vol.21, pp.19, 2019, https://doi.org/10.1021/acs.orglett.9b02729