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

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

Original languageEnglish (US)
Pages (from-to)3881-3887
Number of pages7
JournalJournal of Organic Chemistry
Volume49
Issue number21
DOIs
Publication statusPublished - Oct 1984

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ASJC Scopus subject areas

  • Organic Chemistry

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