quinine carbon atom numbering scheme left and asymmetric centers right
The total synthesis of quinine, a naturally-occurring antimalarial drug, was developed over a 150-year period. The development of synthetic quinine is considered a milestone in organic chemistry although it has never been produced industrially as a substitute for natural occurring quinine. The subject has also been attended with some controversy: Gilbert Stork published the first stereoselective total synthesis of quinine in 2001, meanwhile shedding doubt on the earlier claim by Robert Burns Woodward and William Doering in 1944, claiming that the final steps required to convert their last synthetic intermediate, quinotoxine, into quinine would not have worked had Woodward and Doering attempted to perform the experiment. A 2001 editorial published in Chemical & Engineering News sided with Stork, but the controversy was eventually laid to rest once and for all when Williams and coworkers successfully repeated Woodward's proposed conversion of quinotoxine to quinine in 2007.[1]
^Smith, Aaron C.; Williams, Robert M. (2008-02-15). "Rabe Rest in Peace: Confirmation of the Rabe–Kindler Conversion of d‐ Quinotoxine Into Quinine: Experimental Affirmation of the Woodward–Doering Formal Total Synthesis of Quinine". Angewandte Chemie International Edition. 47 (9): 1736–1740. doi:10.1002/anie.200705421. ISSN 1433-7851. PMC 3085927. PMID 18236503.
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The totalsynthesis of quinine, a naturally-occurring antimalarial drug, was developed over a 150-year period. The development of synthetic quinine is...
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Ishikawa H (November 2019). "Enantioselective totalsynthesis of the unnatural enantiomer of quinine". Chemical Science. 10 (41): 9433–9437. doi:10.1039/c9sc03879e...
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