Quinine is a quinoline alkaloid natural product isolated from the bark of the <i>Cinchona</i> plants (Quina), known for a long time for its intriguing scaffold and anti-malarial activity. Starting from affordable, commercially available isonicotinic acid, the pyridine scaffold was transformed into a functionalized, decorated tetrahydropyridine via a reductive hydroxyalkylation strategy. Subsequent envisioned transformations include intramolecular cyclizing to afford the bicycle motif and asymmetric aldol addition with 6-methoxyquinoline-4-carbaldehyde to complete a novel total synthesis of (−)-Quinine.

Progress towards the total synthesis of (−)-quinine

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