Introduction of a chiral centre on C-6 of a carbohydrate unit: Application to the synthesis of the C-2 to C-15 fragment of ionomycin

Article abstract of DOI:10.1016/S0040-4020(01)87081-2

Glucose is converted into the α,β-unsaturated urono-8,4-lactone 29 using an intramolecular Wadsworth-Emmons reaction. Higher order cuprates add to the lactone to provide the C-6 substituted carbohydrate derivative with high stereoselectivity. This product can be converted into the dithiane 34b which when coupled with an appropriate epoxide yields compound 37 which contains the C-2 to C-15 fragment of ionomycin with the correct absolute stereochemistry at each asymmetric centre for conversion into ionomycin.