Studies in the synthesis of C ring bridged morphinans. 2. The synthesis and structural verification of a novel 3,11c-ethano-10-hydroxy-6-methyl-1,2,3,3a,11b,11c-hexahydroaporphine

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

Research output: Contribution to journalArticle

9 Citations (Scopus)

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 languageEnglish
Pages (from-to)3881-3887
Number of pages7
JournalJournal of Organic Chemistry
Volume49
Issue number21
StatePublished - 1984

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Morphinans
Hydrofluoric Acid
X ray crystallography
Nuclear magnetic resonance
Derivatives
Molecules
bicyclo(2.2.2)oct-2-ene
aporphine
octane

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Studies in the synthesis of C ring bridged morphinans. 2. The synthesis and structural verification of a novel 3,11c-ethano-10-hydroxy-6-methyl-1,2,3,3a,11b,11c-hexahydroaporphine. / Roche, Victoria F.; Roche, Edward B.; Nagel, Donald L.; McPhail, Andrew T.

In: Journal of Organic Chemistry, Vol. 49, No. 21, 1984, p. 3881-3887.

Research output: Contribution to journalArticle

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