Addition of C-nucleophiles to carbohydrate-derived 2,3-dihydro-4H-pyran-4-ones: A new entry to thriomboxane analogues

Article abstract of DOI:10.1016/S0040-4020(97)00475-4

Nucleophilic additions of silyl- and sulfur-stabilized carbanions 5a-e to carbohydrate-derived 2,3-dihydro-4H-pyran-4-ones 4a,b are described. Depending on the combination of substituents attached to the C₁-anion, either 1,2- or 1,4-adducts are preferentially formed. Coupling of vinyl cuprate derived from 16 with enone 4a stereoselectively afforded pyranone 17 which is a potential precursor for thromboxane analogues.