Structure and absolute configuration of versiol, a metabolite from Aspergillus versicolor

Abstract

X-Ray analysis has established the structure and absolute configuration of versiol (1), a metabolite isolated from Aspergillus versicolor. Crystals are orthorhombic, space group P2₁2₁2₁, with a= 9.140(3), b= 6.118(2), c= 25.201(7)Å, Z= 4. The structure was solved by direct methods and refined by least-squares techniques to R 0.048 for 1 249 reflections. The absolute configuration determined by the Bijvoet method has verified that assigned by application of the Horeau asymmetric synthesis, but shown that that assigned by taking into account the Cotton effect was incorrect. Intermolecular hydrogen bonds link the molecules into infinite chains along the a axis.