One famous synthesis of this molecule relied on the Kondo-Mori vinylic gamma-lactone synthesis and uses a Staudinger ligation and a mesyl leaving group to create a bicyclic moeity.
One famous synthesis of this molecule relied on the Kondo-Mori vinylic gamma-lactone synthesis and uses a Staudinger ligation and a mesyl leaving group to create a bicyclic moeity. Another synthesis uses Hoffman elimination to create the vinyl group, and replaces an amide with a benzyl in order to facilitate a final Claisen condensation. Jacobsen's synthesis makes a boronic ester from piperidine, followed by coupling and a Sharpless reaction to form a cyclizable epoxide. The first method of synthesizing it uses hypobromite in the first step and reduces the penultimate ketone via aluminum, performed by Rabe and Kindler. Stork's stereoselective synthesis of this compound is remarkable due to its four stereocenters, and it was first isolated from the cinchona tree. Containing a fused pyridine and anisole, for 10 points, name this compound synthesized by Doring and Woodward, which was originally used to treat a disease caused by Plasmodium, malaria.
One famous synthesis of this molecule relied on the Kondo-Mori vinylic gamma-lactone synthesis and uses a Staudinger ligation and a mesyl leaving group to create a bicyclic moeity.
{Quinine}