X-Ray crystal structure and absolute configuration of the fungal phenalenone herqueinone
Abstract
The relative and absolute configurations of the two chiral centres of herqueinone (3) have been determined by X-ray crystallographic analysis; a biosynthetic mechanism is proposed for the formation of the centre at C(2′) the stereospecificity of which is predetermined by the configuration of an intermediate containing an inverted isoprene unit at a transitory C(5) chiral centre.