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Ho Kenny Park K, Chen R, Chen DY. Programmed serial stereochemical relay and its application in the synthesis of morphinans. Chem Sci. 2017;8(10):7031-7037doi: 10.1039/c7sc03189k.
Ho Kenny Park, K., Chen, R., & Chen, D. Y. (2017). Programmed serial stereochemical relay and its application in the synthesis of morphinans. Chemical science, 8(10), 7031-7037. https://doi.org/10.1039/c7sc03189k
Ho Kenny Park, Kun, et al. "Programmed serial stereochemical relay and its application in the synthesis of morphinans." Chemical science vol. 8,10 (2017): 7031-7037. doi: https://doi.org/10.1039/c7sc03189k
Ho Kenny Park K, Chen R, Chen DY. Programmed serial stereochemical relay and its application in the synthesis of morphinans. Chem Sci. 2017 Oct 01;8(10):7031-7037. doi: 10.1039/c7sc03189k. Epub 2017 Aug 30. PMID: 29147530; PMCID: PMC5642196.
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Chem Sci. 2017 Oct 01;8(10):7031-7037. doi: 10.1039/c7sc03189k. Epub 2017 Aug 30.

Programmed serial stereochemical relay and its application in the synthesis of morphinans.

Chemical science

Kun Ho Kenny Park, Rui Chen, David Y-K Chen

Affiliations

  1. Department of Chemistry , Seoul National University , Gwanak-1 Gwanak-ro, Gwanak-gu , Seoul 151-742 , South Korea . Email: [email protected].

PMID: 29147530 PMCID: PMC5642196 DOI: 10.1039/c7sc03189k

Abstract

Herein we report a rationally designed, serial point-to-axial and axial-to-point stereoinduction and its integration into multi-step and target-oriented organic synthesis. In this proof-of-concept study, the configurational stability of several carefully designed atropisomeric intermediates and the fidelity of their unconventional stereoinductions were systematically investigated. The highly functionalized prepared synthetic intermediate was further applied in a novel chemical method to access the morphinans and it is potentially applicable to other structurally related alkaloids.

References

  1. J Am Chem Soc. 2009 Aug 19;131(32):11402-6 - PubMed
  2. Org Lett. 2014 Oct 17;16(20):5282-5 - PubMed
  3. Chemistry. 2017 May 23;23 (29):6993-6995 - PubMed
  4. J Am Chem Soc. 2002 Dec 11;124(49):14542-3 - PubMed
  5. Angew Chem Int Ed Engl. 2002 Jun 17;41(12):2008-22 - PubMed
  6. Org Lett. 2010 Mar 5;12(5):1072-5 - PubMed
  7. Org Lett. 2010 Oct 1;12(19):4224-7 - PubMed
  8. J Chem Soc Perkin 1. 1967;2:128-32 - PubMed
  9. Org Lett. 2005 Jun 23;7(13):2531-4 - PubMed
  10. J Am Chem Soc. 2002 Oct 23;124(42):12416-7 - PubMed
  11. Angew Chem Int Ed Engl. 2011 Apr 18;50(17 ):3892-4 - PubMed
  12. J Org Chem. 2006 Jan 20;71(2):449-55 - PubMed
  13. J Med Chem. 1976 Oct;19(10):1171-5 - PubMed
  14. Chem Ber. 1967;100(5):1550-8 - PubMed
  15. Angew Chem Int Ed Engl. 2014 Apr 22;53(17):4355-8 - PubMed
  16. J Org Chem. 1998 Aug 21;63(17):5908-5918 - PubMed
  17. Org Lett. 2006 Nov 9;8(23):5311-3 - PubMed
  18. Chemistry. 2013 Jan 2;19(1):264-9 - PubMed
  19. Angew Chem Int Ed Engl. 2016 Nov 7;55(46):14306-14309 - PubMed
  20. Chemistry. 2015 Nov 9;21(46):16379-82 - PubMed
  21. Org Lett. 2014 Dec 5;16(23):6244-7 - PubMed
  22. J Am Chem Soc. 2005 Oct 26;127(42):14785-803 - PubMed
  23. J Am Chem Soc. 2002 Feb 6;124(5):773-5 - PubMed
  24. Chem Asian J. 2013 Jun;8(6):1105-9 - PubMed
  25. Chem Asian J. 2010 Oct 4;5(10):2192-8 - PubMed
  26. Chemistry. 2008;14(22):6606-8 - PubMed
  27. Chem Soc Rev. 2013 Nov 7;42(21):8434-66 - PubMed
  28. J Am Chem Soc. 1975 Mar 5;97(5):1239-40 - PubMed
  29. Angew Chem Int Ed Engl. 2014 Dec 1;53(49):13498-501 - PubMed
  30. J Chem Soc Perkin 1. 1969;15:2030-3 - PubMed
  31. J Am Chem Soc. 2016 Dec 21;138(50):16553-16560 - PubMed
  32. J Org Chem. 2004 Dec 10;69(25):8836-41 - PubMed
  33. Org Lett. 2017 Feb 3;19(3):532-535 - PubMed
  34. J Org Chem. 2016 Nov 18;81(22):10930-10941 - PubMed
  35. Org Lett. 2008 Mar 20;10 (6):1243-6 - PubMed
  36. J Am Chem Soc. 2009 Nov 11;131(44):16045-7 - PubMed
  37. Acc Chem Res. 2002 Oct;35(10):856-66 - PubMed
  38. J Med Chem. 2015 Jun 25;58(12):5038-52 - PubMed
  39. J Med Chem. 1976 Oct;19(10):1175-80 - PubMed

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