Strictly strychnine

A concise six-step synthesis by Christopher Vanderwal and colleagues at the University of California, Irvine uses readily available materials to generate the infamous poison strychnine. Their approach puts a new twist on some well-known chemistry. Vanderwal and colleagues explain how two previous approaches to strychnine have successfully exploited the Diels-Alder cycloaddition reaction. However, the researchers knew that tryptamine-derived Zincke aldehyde could be used to shorten the reaction scheme. Their Zincke aldehyde approach places appropriate groups in the right place and in the appropriate oxidation state for the final step to product. While yield is not exceptional, they emphasise how a mere four chemical steps are needed to create four new carbon-carbon bonds and one carbon-oxygen bond, generating a five-carbon donor-acceptor diene for the Diels-Alder step.