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
APA
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MLA
NLM
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 VF, Roche EB, Nagel DL, Mcphail AT. 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. 1984 Jan 1;49(21):3881–7.
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.
Roche VF, Roche EB, Nagel DL, Mcphail AT. 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. 1984 Jan 1;49(21):3881–3887.
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