The featured molecules this month come from the article “The
Conversion of Carboxylic Acids to Ketones: A Repeated Discovery” by
John W. Nicholson and Alan D. Wilson. The authors describe the repeated “discovery” of
this reaction and illustrate its central role in Woodward’s total
synthesis of strychnine. Strychnine is a member of a large class of nitrogen
heterocycles known as alkaloids, a name derived from the fact that all
produce basic solutions in water. Other well-known members of this class
of compounds, all of which are pharmacologically active, are nicotine,
atropine (deadly nightshade), quinine, lysergic acid, cocaine, and the
three structurally similar compounds codeine, heroin, and morphine.
In addition to the static image, two fully manipulable versions (Jmol, MDLChime) of these molecules appear below. (The Jmol versions may take a few extra seconds to load, based on the speed of your Internet connection.)
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