Synthesis of Stereodefined Z-vinyl Iodides from Carbohydrates as a Prelude to C/D Ring Assembly in Taxanes
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.
Vinyl iodides such as (−)-10 and (+)-20 have been prepared from D-mannitol and D-glucose, respectively.
Hofferberth, John E. and al., et, "Synthesis of Stereodefined Z-vinyl Iodides from Carbohydrates as a Prelude to C/D Ring Assembly in Taxanes" (1999). Tetrahedron Letters 40(18): 3519-3522. Faculty Publications. Paper 29.