Publications [#233457] of Andrew T. McPhail

Journal Articles

  1. Brambilla, R; Friary, R; Ganguly, A; Puar, MS; Topliss, JG; Watkins, R; McPhail, AT, "A Stereochemical Model of the Veratrum Alkaloids", Journal of Organic ChemistryJanuary,, 1982, 47(21), 4137-4145, American Chemical Society (ACS) [Gateway.cgi], [doi].
    (last updated on 2026/01/21)

    Abstract:
    A stereoselective synthesis beginning from the tetracyclic isoxazolidine 3 gave an inactive model (2) of rings D–F of the hypotensive Veratrum alkaloids (1). Cleaving, N-demethylating, and epimerizing 3 gave the amino alcohol 5a. Diazotizing 5a afforded lactamdiol 10, which retained the configuration of the carbinamine carbon of 5a. Reduction of the lactam of 10 yielded 2. Single-crystal X-ray analysis of 2 confirmed the assignment of relative stereochemistry at C6a and C11 of 2 and established that the solid-state conformation was all-chair. © 1982, American Chemical Society. All rights reserved.