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Studies in the Synthesis of C Ring Bridged Morphinans. 2.1 The Synthesis and Structural Verification of a Novel 3, llc-Ethano-10-hydroxy-6-methyl-l, 2, 3, 3a, llb, llc-hexahydroaporphine

Publication ,  Journal Article
Roche, VF; Roche, EB; Nagel, DL; Mcphail, AT
Published in: Journal of Organic Chemistry
January 1, 1984

The title compound and its 10-methoxy congener were prepared from bicyclo[2. 2. 2]oct-2-ene in approximately 2% overall yield. In the course of the synthesis of the final product, 14 novel bicyclo[2. 2. 2]-and-[3.2.1]octane derivatives were isolated and characterized. Entry into the aporphine ring system was accomplished by cyclizing the appropriate N-formylisoquinoline precursor with liquified hydrofluoric acid which gave the bridged 6-fonnyl-10-methoxyhexahydroaporphine molecule in essentially quantitative yield. Structural verification of the final product was through 13C 1H and NMR and X-ray crystallography. © 1984, American Chemical Society. All rights reserved.

Duke Scholars

Published In

Journal of Organic Chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

January 1, 1984

Volume

49

Issue

21

Start / End Page

3881 / 3887

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

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Roche, V. F., Roche, E. B., Nagel, D. L., & Mcphail, A. T. (1984). Studies in the Synthesis of C Ring Bridged Morphinans. 2.1 The Synthesis and Structural Verification of a Novel 3, llc-Ethano-10-hydroxy-6-methyl-l, 2, 3, 3a, llb, llc-hexahydroaporphine. Journal of Organic Chemistry, 49(21), 3881–3887. https://doi.org/10.1021/jo00195a002
Roche, V. F., E. B. Roche, D. L. Nagel, and A. T. Mcphail. “Studies in the Synthesis of C Ring Bridged Morphinans. 2.1 The Synthesis and Structural Verification of a Novel 3, llc-Ethano-10-hydroxy-6-methyl-l, 2, 3, 3a, llb, llc-hexahydroaporphine.” Journal of Organic Chemistry 49, no. 21 (January 1, 1984): 3881–87. https://doi.org/10.1021/jo00195a002.
Roche, V. F., et al. “Studies in the Synthesis of C Ring Bridged Morphinans. 2.1 The Synthesis and Structural Verification of a Novel 3, llc-Ethano-10-hydroxy-6-methyl-l, 2, 3, 3a, llb, llc-hexahydroaporphine.” Journal of Organic Chemistry, vol. 49, no. 21, Jan. 1984, pp. 3881–87. Scopus, doi:10.1021/jo00195a002.
Journal cover image

Published In

Journal of Organic Chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

January 1, 1984

Volume

49

Issue

21

Start / End Page

3881 / 3887

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry