Functionalised carbocycles from carbohydrates. Part 7. A route to carbacyclin from a D-glucose derivative. X-Ray crystal structure of 3-endo-benzoyloxy-2-exo-(1,3-diphenyl-1,3,2-diazaphospholan-2-yloxymethyl)-6-oxobicyclo[3.3.0]-octane

Abstract

A specific method for converting the epoxide (7), which was previously obtained from methyl α-D-glucopyranoside, into the prostaglandin intermediate (1) is described, and a route from this latter compound into the previously reported bicyclo[3.3.0]octan-3-one (4) has been developed (using racemic material). Compound (4) is a synthetic precursor of carbacyclin and its analogues. In the course of this work a functionalised bicyclo[3.3.0]octan-2-one was encountered; it was characterised by X-ray diffraction analysis of the derivative (19).