Robert B. Woodward The UV absorption of<unk>  peaks around 350 nm (in UVA). Fluorescent emission peaks at around 460 nm (bright blue/cyan hue).<unk>  is highly fluorescent (quantum yield ~0.58) in 0.1 M sulfuric acid solution. The 3D structure of<unk>  can be viewed using QRChem.net. Synthesis Cinchona trees remain the only economically practical source of<unk> . However, under wartime pressure during World War II, research towards its synthetic production was undertaken. A formal chemical synthesis was accomplished in 1944 by American chemists R.B. Woodward and W.E. Doering. Since then, several more efficient<unk>  total syntheses have been achieved, but none of them can compete in economic terms with isolation of the alkaloid from natural sources. The first synthetic organic dye, mauveine, was discovered by William Henry Perkin in 1856 while he was attempting to synthesize<unk> . Biosynthesis<unk>  biosynthesis In the first step of<unk>  biosynthesis, the enzyme strictosidine synthase catalyzes a stereoselective Pictet–Spengler reaction between tryptamine and secologanin to yield strictosidine. Suitable modification of strictosidine leads to an aldehyde. Hydrolysis and decarboxylation would initially remove one carbon from the iridoid portion and produce corynantheal. Then the tryptamine side-chain were cleaved adjacent to the nitrogen, and this nitrogen was then bonded to the acetaldehyde function to yield cinchonaminal. Ring opening in the indole heterocyclic ring could generate new amine and keto functions. The new quinoline heterocycle would then be formed by combining this amine with the aldehyde produced in the tryptamine side-chain cleavage, giving cinchonidinone. For the last step, hydroxylation and methylation gives<unk> . Catalysis Due to their high selectivity<unk>  – and Cinchona alkaloids in general – are promising catalysts for synthesis. Russo et al., 2009 employ<unk>  to add a malononitrile to α,β-enones via a Michael addition.
Quinine
Artemether
Delamanid
Ajmalicine
Pyrimethamine
Chloroquine
Mefloquine
Primaquine