Publications [#233430] of Andrew T. McPhail

Journal Articles

  1. 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 ChemistryJanuary,, 1984, 49(21), 3881-3887, American Chemical Society (ACS) [Gateway.cgi], [doi].
    (last updated on 2026/01/21)

    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. © 1984, American Chemical Society. All rights reserved.