Title

Synthesis of Stereodefined Z-vinyl Iodides from Carbohydrates as a Prelude to C/D Ring Assembly in Taxanes

Document Type

Article

Publication Date

4-30-1999

Abstract

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.

Journal

Tetrahedron Letters

Volume

40

Issue

18

First Page

3519

Last Page

3522