SYNTHESIS AND ABSOLUTE STRUCTURE DETERMINATION OF CAMPHANOATE DERIVATIVES OF 5 BICYCLO[3.1.0]HEXANE COMPOUNDS

The relative and absolute stereochemistry of five compounds, 2-acetoxy -3,3-dimethylbicyclo[3.1.0]hexan-exo-4-yl camphanoate, C20H28O6, (I), xy-3,3,exo-6-trimethylbicyclo[3.1.0]hexan-exo-4-yl camphanoate, C21H30 O6, (II), (1R,2S,4R,5S, xy-3,3,exo-6-trimethylbicyclo[3.1.0]hexan-exo- 4-yl camphanoate, C21H30O6, (III), l)-3,3,exo-6-trimethylbicyclo[3.1.0 ]hexan-exo-4-yl camphanoate, C25H36O6, (IV), and 4R,5R,6S)endo-2-aceto xy-3,3,exo-6-trimethylbicyclo [3.1.0]hexan-endo-4-yl camphanoate, C21H 30O6, (V), (camphanoate is yl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbo xylate) have been determined and the conformation of the five-membered ring of each one is discussed. These compounds were synthesized by an enantioselective esterase-catalysed hydrolysis followed by acylation with camphanoyl chloride.