Conversion of Carbohydrates into Functionalised Carbocyclic Compounds

Abstract

Mercury containing derivatives of a hex-5-enopyranoside have been studied as possible precursors of functionalised cyclopentanes. They were found not to be useful for this purpose but such compounds were synthesised from an acyclic hex-5-enose derivative and these have led to an enantiomerically pure prostaglandin precursor and hence a new route to prostaglandins has been opened. As the result of the above work, an efficient route to (+)-exo-brevicomin, the sex-pheromone of Western pine beetles, was developed and a second route to prostaglandins via compounds with bicyclo [3.2.0] heptane ring systems was explored. A novel synthesis of a "pseudotrisaccharide", which is related to aminoglycoside antibiotics, has been completed by using three key reactions that have been discovered in this laboratory.