Showing papers on "Wieland–Miescher ketone published in 2003"
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TL;DR: In this paper, the Wieland-Miescher ketone, its C(5) homologue, and their C(1) dioxolane derivatives were studied on commercially available polysaccharide-based chiral stationary phases (CSPs).
Abstract: The direct HPLC resolution of four structurally related compounds, the Wieland‐Miescher ketone, its C(5) homologue, and their C(1) dioxolane derivatives, was studied on commercially available polysaccharide‐based chiral stationary phases (CSPs) cellulose tris‐(3,5‐dimethylphenylcarbamate) (Chiralcel OD‐H), native β‐cyclodextrin (Cyclobond I), and acetylated, carboxymethylated and permethylated β‐cyclodextrins. The retention, resolution, and elution sequence of the enantiomeric couples were compared using different mobile phases. Baseline enantioseparation of all examined compounds was achieved only on the carboxymethyl‐derivatized β‐cyclodextrin stationary phase that appeared the most effective chiral selector for this class of compounds. Native, acetylated‐, and permethylated‐β‐cyclodextrin CSPs exhibited specific selectivity providing, in general, partial resolution of the compounds under investigation. On Chiralcel OD‐H, only two enantiomeric couples were fully separated. Elution orders depend...
10 citations
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TL;DR: A novel synthesis of the title compound has been accomplished starting with alcohol (3) which in turn was prepared from the Wieland-Miescher ketone (1), which after reduction, mesylation, and demesylation afforded the unsaturated ester as discussed by the authors.
2 citations