Recent advances in Cinchona alkaloid chemistry

Quinine has been among the best known alkaloids for over 300 years, thanks to its antimalarial activity. In the last two decades, Cinchona alkaloids have emerged as powerful chiral auxiliaries, resulting in some well known landmark developments in asymmetric synthesis, but more recently these alkaloids themselves have been shown to undergo some remarkable transformations and skeletal shifts that are rapidly widening perspectives in the chemistry of Cinchona bases, embracing both basic and applied science. The alkaloids enter into a series of fundamental transformations that have given rise to the industrial manufacture of a host of new enantiopure materials showing promise for asymmetric syntheses and combinatorial chemistry. Stereochemical diversity, well developed conformational minima not encountered in conventional organic substrates, hydrophilic pockets and stereoelectronics contribute subtle mechanistic features and structural complexity. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).