D-(-)-quinic acid: a chiron store for natural product synthesis

Chemists have long been aware of the potential advantages of using chiral building blocks as starting materials in the synthesis of natural products. D-(-)-Quinic acid 1, a widely occurring plant metabolite, has seen in the past only limited use as an optically active synthetic precursor in multistep chemical synthesis but has been particularly appreciated for the preparation of natural compounds featuring cyclohexane substituted skeletons. More recently, its applications as a chiral template in natural product synthesis have been rapidly growing, the serviceability of this highly functionalized substrate being easily extended to the preparation of open chain building blocks, which could be further transformed into optically active cyclopentane substituted skeletons and nitrogen containing targets. This review comprehensively covers quinic acid chemistry literature up to the beginning of 1997 and is aimed at stimulating the development of new chiral building blocks from a readily available, inexpensive starting material. (C) 1997 Elsevier Science Ltd.