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

Victoria F. Roche; Edward B. Roche; Donald L. Nagel; Andrew T. Mcphail

doi:10.1021/jo00195a002

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

Victoria F. Roche, Edward B. Roche, Donald L. Nagel, Andrew T. Mcphail

Department of Pharmacy Sciences

Research output: Contribution to journal › Article

9 Scopus citations

Abstract

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-formyl-10-methoxyhexahydroaporphine molecule in essentially quantitative yield. Structural verification of the final product was through ¹³C and ¹H NMR and X-ray crystallography.

Original language	English (US)
Pages (from-to)	3881-3887
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	49
Issue number	21
DOIs	https://doi.org/10.1021/jo00195a002
State	Published - Oct 1984

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00195a002

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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

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. / Roche, Victoria F.; Roche, Edward B.; Nagel, Donald L.; Mcphail, Andrew T.

In: Journal of Organic Chemistry, Vol. 49, No. 21, 10.1984, p. 3881-3887.

Research output: Contribution to journal › Article

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abstract = "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-formyl-10-methoxyhexahydroaporphine molecule in essentially quantitative yield. Structural verification of the final product was through 13C and 1H NMR and X-ray crystallography.",

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AB - 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-formyl-10-methoxyhexahydroaporphine molecule in essentially quantitative yield. Structural verification of the final product was through 13C and 1H NMR and X-ray crystallography.

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