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Download Hi-Res ImageDownload to MS-PowerPointCite This:Org. Lett. 2018, 20, 6, 1559-1562
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Favorskii-Type Rearrangement of the 4,5-Epoxymorphinan Skeleton

  • Noriki Kutsumura
    Noriki Kutsumura
    International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8575, Japan
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    Orcidhttp://orcid.org/0000-0002-1494-2133
    • , 
  • Yasuaki Koyama
    Yasuaki Koyama
    Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan
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    • , 
  • Yuko Suzuki
    Yuko Suzuki
    Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan
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    • , 
  • Ken-ichi Tominaga
    Ken-ichi Tominaga
    National Institute of Advanced Industrial Science and Technology (AIST), Central 5 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan
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    Orcidhttp://orcid.org/0000-0002-6078-2169
    • , 
  • Naoshi Yamamoto
    Naoshi Yamamoto
    International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8575, Japan
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    • , 
  • Tsuyoshi Saitoh
    Tsuyoshi Saitoh
    International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8575, Japan
    More by Tsuyoshi Saitoh
    • , 
  • Yasuyuki Nagumo
    Yasuyuki Nagumo
    International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8575, Japan
    More by Yasuyuki Nagumo
    • , and 
  • Hiroshi Nagase*
    Hiroshi Nagase
    International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8575, Japan
    Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan
    *E-mail: [email protected]
    More by Hiroshi Nagase
    Orcidhttp://orcid.org/0000-0003-0428-3979
Cite this: Org. Lett. 2018, 20, 6, 1559–1562
Publication Date (Web):March 7, 2018
https://doi.org/10.1021/acs.orglett.8b00288
Copyright © 2018 American Chemical Society
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Abstract

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The aldol condensation of naltrexone with various aryl aldehydes gives the corresponding 7-benzylidenenaltrexone derivatives in high yields. However, novel C-ring-contracted morphinan compounds were produced when 2-pyridinecarboxaldehyde or its related analogues were used as a coupling partner. The key structural feature was the existence of the tetrahydrofuran ring (4,5-epoxy ring, E-ring) of the morphinan skeleton. The time-resolved in situ IR spectroscopy of the reaction system indicated the short-lived absorption of the distorted cyclopropanone intermediate.

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  • Experimental procedures, characterization data, 1H and 13C NMR spectra of all new compounds, and DFT calculations (PDF)

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Cited By

This article is cited by 5 publications.

  1. . Rearrangement Reactions. 2021,,, 1-68. https://doi.org/10.1002/9783527828166.ch1
  2. Surya K. De. Applied Organic Chemistry. 2021,,https://doi.org/10.1002/9783527828166
  3. Natalia A. Danilkina, Anna A. Vasileva, Irina A. Balova. A.E.Favorskii’s scientific legacy in modern organic chemistry: prototropic acetylene – allene isomerization and the acetylene zipper reaction. Russian Chemical Reviews 2020, 89 (1) , 125-171. https://doi.org/10.1070/RCR4902
  4. Hiroshi Nagase, Masahiro Yata, Noriki Kutsumura, Yasuyuki Nagumo, Naoshi Yamamoto, Yukiko Ishikawa, Yoko Irukayama-Tomobe, Masashi Yanagisawa. A Novel Rearrangement Reaction of Morphinan to Arylmorphan Skeletons and the Pharmacologies of Arylmorphan Derivatives. HETEROCYCLES 2019, 99 (1) , 134. https://doi.org/10.3987/COM-18-S(F)53
  5. Noriki Kutsumura, Hiroshi Nagase. Unique Reactions of Morphinan Skeletons and Conversions of the Skeletons to Active Alkaloids. Journal of Synthetic Organic Chemistry, Japan 2018, 76 (9) , 914-921. https://doi.org/10.5059/yukigoseikyokaishi.76.914

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