A selective, practical and scalable aerobic oxidation of alcohols is described using catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and HNO 3 , with molecular oxygen serving as the terminal oxidant. The method was successfully applied to the oxidation of a wide range of benzylic, propargylic and allylic alcohols, including two natural products, namely carveol and podophyllotoxin. The conditions are also applicable to the selective oxidative deprotection of PMB ethers.

This work describes the process development and manufacture of an ampakine-type active pharmaceutical ingredient in clinical trials. A regioselective CDI-mediated amidation process was optimized for the subsequent couplings of two distinctive amines with a terephthalic acid substrate. Choice of the synthetic route, key scale-up issues, safety calorimetry, and optimization of all steps for multikilogram production are discussed.