De novo approach to C-6 substituted hexoses

ORGN 675

Qi Zhang, qzhang4@mix.wvu.edu1, George A. O'Doherty, george.odoherty@mail.wvu.edu2, Mingde Shan, mingdeshan@yahoo.com.cn3, and Yalan Xing, yxing@mix.wvu.edu1. (1) C. Eugene Bennett Department of Chemistry, West Virginia University, 217 Clark Hall Prospect St., Morgantown, WV 26505, (2) C. Eugene Bennett Department of Chemistry, West Virgnia University, 284 Prospect Street, 217 Clark Hall, Morgantown, WV 26506, (3) C. Eugene Bennett Department of Chemistry, West Viginia University, Morgantown, WV 26505
The enantioselective synthesis of various C-6 substituted hexoses has been achieved in 4 steps. The succinct route relies on the highly enantioselective Noyori reduction, Achmatowicz reaction (an oxidative rearrangement of furfuryl alcohols to pyranones) and subsequent diastereoselective oxidation and reduction reactions.