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They were right after all
Date:1/31/2008

This release is also available in German.

Drugs derived from cinchona bark, known as cinchona alkaloids, have been used in healing from ancient times. The most prominent representative of this group is quinine, a bitter substance contained in beverages such as tonic water and used in modern medicine to combat malaria. As early as 1945, Robert Burns Woodward and William von Eggers Doering (Harvard University) described how to synthesize quinine in the laboratory. The last step of this formal total synthesis, a three-step reaction procedure previously described by Paul Rabe and Karl Kindler in 1918, has continued to be the subject of much controversy to this day. Aaron C. Smith and Robert M. Williams at Colorado State University (USA) have now successfully reproduced the RabeKindler protocol. As described in an Angewandte Chemie article dedicated to Doering on his 90th birthday, they repeated the entire procedure without employing any modern methods.

Had they done it or not? That has been the question for decades. Woodward and Doering published the synthesis of d-quinotoxine in 1944. Based on the conversion of d-quinotoxine into quinine described by Rabe and Kindler in 1918, they claimed to have derived the total synthesis of quinine, though they had not actually completed this last step themselves before publishing. Their formal total synthesis was strongly challenged and was even dismissed as a myth by Gilbert Stork (Columbia University) in 2001.

Quinine and the cinchona bark alkaloids play an important role in modern medicine. It is thus amazing that no attempts to reproduce the RabeKindler conversion of quinotoxine into quinine have been published, marvels Williams. Smith and Williams reviewed the old publications, researched further references, and set themselves the task of repeating the procedure outlined by Rabe and Kindlerand with te
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Contact: Robert M. Williams
rmw@chem.colostate.edu
970-491-6747
Wiley-Blackwell
Source:Eurekalert

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