Structure of a model for the aranorosin nucleus

Abstract

The structure of a synthetic model system, 2-hydroxy-6,7;9,10-cis,cis-diepoxy-1-oxaspiro[4.5]decan-8-one, C 9 H 10 O 5 , for the spirocyclic headgroup of the natural product aranorosin has been determined and shown to possess the natural product stereochemistry. Two crystallographically independent molecules cocrystallize in a centrosymmetric space group. The syn arrangement of the diepoxides and the lactol O atom about the cyclohexanone ring has been confirmed in both molecules. The cyclohexanone ring adopts a boat conformation with the carbonyl O atom anti to the lactol O atom