Publications [#233287] of Andrew T. McPhail

Journal Articles

  1. Nakano, T; Maillo, MA; Usubillaga, A; McPhail, AT; McPhail, DR, "Rearrangements of Derivatives of Methyl 9,11-Dihydroxy-(-)-kauran-19-oate to New Skeletal Diterpenes", Nat. Prod. Letters, 1993, 1(4), 257-262, Informa UK Limited [doi].
    (last updated on 2026/01/21)

    Abstract:
    The acid-catalyzed rearrangement of the 11α-acetoxy-9a-hydroxy derivative (8) of methyl (-)-kaur-9(11)-en-19-oate (1) afforded compound (2) the C/D ring system of which is analogous to that of antheridiogen, Aan (3), the antheridium-inducing factor from Anemia phyllitidis. On the other hand, the rearrangement of the 9α,11α-dihydroxy derivative (9) under identical conditions led to a mixture of compounds (6) and (11). The 9a-hydroxy-llα-methanesulfonyloxy derivative (12) underwent a pinacolic-type rearrangement with potassium t-butoxide in t-butanol to give a ring B-homo derivative (13). © 1993, Taylor & Francis Group, LLC. All rights reserved.