ChemInform Abstract: Enantioselective Synthesis Through Microbial Oxidation of Arenes. Part 1. Efficient Preparation of Terpene and Prostanoid Synthons.

Abstract

325ChemInform Abstract Enantioselective oxidation of the benzenes (I) affords the cis diols (II), whose utility in the synthesis of optically pure natural products is discussed (yields in g). The toluenediol (IIa) is converted in three steps to the enone (VI), which is a known precursor of the prostaglandin PGE2α (VII). In the second generation synthesis an overall yield of 45% is reached for this enone starting from toluene (Ia). A method for reliable oxidative cleavage of 1,3-dienes such as (IX) to 1,4-dicarbonyl compounds such as (VIII) or (X) s implemented. Other transformations of (IIa) leading to the terpenoid or cyclohexene oxide synthons (XI)-(XIII) are discussed.