Laurencia natural products, part II. Crystal structure and absolute stereochemistry of laurinterol acetate, A bicyclo[3,1,0]hexane derivative

Abstract

The crystal structure and the absolute stereochemistry of laurinterol acetate, a crystalline derivative of laurinterol, have been determined by a single-crystal X-ray analysis using three-dimensional diffractometer data. The crystals are monoclinic, space group P2₁, with Z= 2 in a unit cell of dimensions a= 10·26, b= 7·28, c= 12·22 Å, β= 114·1°. The structure was solved by the heavy-atom method and refined by least-squares calculations to R 0·086 for 1097 data. The absolute stereochemistry of the related compound aplysin has been established by consideration of anomalous dispersion effects. Laurinterol contains a trisubstituted bicyclo[3,1,10]hexane system which adopts an overall boat-like conformation.