Chiral building units from carbohydrates-XIII. Identification of the absolute configuration of endo-brevicomin from dendroctonus frontalis and synthesis of both enantiomers from d-ribose

Article abstract of DOI:10.1016/S0040-4020(01)86784-3

The synthesis of both enantiomers of endo-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.l]octana (endo-brevicomin, 12 and 12a) starting froni D-ri-bose is described. Key interinediate is the open chain derivative 7, a chiral building unit easily available from ca