Publications [#233406] of Andrew T. McPhail

Journal Articles

  1. Nakano, T; Hernández, MI; Polachini, JM; Peña, DA; Corothie, E; Rojas, A; McPhail, AT, "Oxidation of methyl podocarpate and methyl 12-hydroxyabietan-8,11,13-trien-18-oate with thallium(III) perchlorate", Journal of the Chemical Society Perkin Transactions 1January,, 1986(10), 1727-1731, Royal Society of Chemistry (RSC) [Gateway.cgi], [doi].
    (last updated on 2026/01/21)

    Abstract:
    On oxidation with thallium(III) perchlorate in aqueous perchloric acid, methyl podocarpate (5) yielded two products which were identified on the basis of spectral data as the p-quinol (8) and the aryl ketone (7a) which resulted from oxidation at C-7 remote from the aromatic ring c. When methyl 12-hydroxyabietan-8,11,13-trien-18-oate (6) was treated with the same reagent, a similar benzylic oxidation occurred yielding two aromatic compounds which spectroscopic analysis showed to be the aryl ketone (11) and the lactone (12) with a rearranged skeleton. The structure and stereochemistry of the latter product were established unequivocally by an X-ray crystallographic analysis. Possible mechanisms for the formation of compounds (7a), (11), and (12) are proposed. © Royal Society of Chemistry.