Chincona

Woodward achieved his first signal success of a lifetime devoted to the preparation of increasingly complex natural products by total synthesis by the successful preparation of quinine. Despite its elegance, this synthesis did not provide a commercially viable alternative to isolation of the drug from chincona bark. A rather short synthesis for this drug from readily available starting materials has been only recently developed by the group at Hoffmann-LaRoche. (The economics of this synthesis are,... 

The quantitative analysis of Chincona bark by the classical methods of titrimetry, gravimetry, and polarimetry has been performed for many years in order to ascertain its commercial value. These compounds have been analyzed by GC, GC-MS, TLC, and mainly HPLC (353-361) with UV or electrochemical detection. Ion-pair HPLC was also used with UV or fluorescence detection by Jeuring et al. (357). Photoreactions of Qn in aqueous citric acid solution have been studied by Laurie et al. (358). After isolation of the components by HPLC and TLC, different spectroscopic techniques (MS, NMR, IR) were used to identify the photoproducts. 

There are no very recent papers dealing with Chincona alkaloid determination in the literature. Table 8 reports some of the most significant works in this field. 

M. Lammerhofer and W. Lindner, Quinince and quinidine derivatives as chiral selectors. Beush type chiral stationary phases for high performance liquid chromatography based on chincona carbamates and their applications as chiral anion exchanger, J. Chromatogr. 741 (1966), 33. 

Karl Anker Jorgensen of Aarhus University, Denmark used Chem. Commun. 2008, 5827) a Chincona based catalyst to effect enantioselective addition of 33 to 34. Enantioselective reduction of the ketone 35 to the alcohol followed by conversion of the nitro group to the alcohol led to IM-2 36, an autoregulator derived from Streptomyces. 

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