APPLICATIONS OF ENZYMES IN THE SYNTHESIS OF BIOACTIVE POLYOLS

Cyclopentadiene, benzene and cycloheptatriene were transformed to functionalized meso-diols. The resulting meso-diols or their corresponding meso-diacetates were subjected to enzymatic asymmetrizations using enzymes, particularly lipases, in organic or aqueous media. Examples of the use of the resulting aracemic products in the synthesis of a variety of polyols of biological interest are reviewed. We are engaged in a program of synthesis of bioactive molecules by routes involving the following features: Readily available cyclic starting materials are subjected to stereospecific oxidation reactions which serve to set relative ring stereochemistry and produce compounds of the stereochemical class meso. These meso compounds are asymmetrized by use of enzymes to set absolute stereochemistry about the ring. Further manipulation then provides useful new chiral pool intermediates which are carried on to target molecules. In many instances, regioselective ring cleavage reactions are used to unveil acyclic compounds with fixed absolute stereochemistry. In this overview of recent efforts from our laboratory we will provide a synopsis of chemoenzyhatic approaches to various bioactive targets utilizing the following as starting materials: