title: Synthesis, stereostructure, and conformations of novel bi- and trifunctional (+)-isomenthone derivatives.
abstract: [reaction: see text] Following protection, keto alcohols 4 [from (+)-isomenthone] undergo reduction to 1,3-diol 6 (S configuration at the new stereocenter). Organometallic C-nucleophiles add to the carbonyl with the same facial selectivity as hydride, providing multifunctional derivatives, e.g., 8 and 9, with five contiguous stereocenters. The side chain hydroxyl of 4 is elaborated into amino and amide derivatives (e.g., 12). Structural analysis shows that 6, 8, 9, and the precursor to 12 (10) all adopt triaxial solid-state conformations.
authors.affiliation: Department of Chemistry, UMIST, Sackville Street, Manchester M60 1QD, UK. john.gardiner@umist.ac.uk
authors.forename: John M
authors.initials: JM
authors.lastname: Gardiner
authors.forename: Philip D
authors.initials: PD
authors.lastname: Crewe
authors.forename: Gillian E
authors.initials: GE
authors.lastname: Smith
authors.forename: Kenneth T
authors.initials: KT
authors.lastname: Veal
authors.forename: Robin G
authors.initials: RG
authors.lastname: Pritchard
authors.forename: John E
authors.initials: JE
authors.lastname: Warren