Synthesis of stereodefined z-vinyl iodides from carbohydrates as a prelude to C/D ring assembly in taxanes

Article abstract of DOI:10.1016/S0040-4039(99)00546-8

D-Mannitol has been transformed into 10 and 14, while D-glucose has served as precursor to 20. In the latter example, key steps include stereocontrolled vinylation, oxidative fragmentation of the tetrahydrofuran- 2,3-diol, oxetane ring closure, and highly stereoselective iodoolefination.