Asymmetric synthesis of furan alcohols

• Online Access: http://hdl.handle.net/2047/D20194402

The importance of the role oligosaccharides play in biological has been becoming more and more apparent. In a commensurate fashion there has been an ever-increasing need for synthetic access to oligosaccharide structure motifs. As these studies have evolved, there has be a change in the desire for specific oligosaccharides produced by natural to structures for structure activity relationship studies. In an effort to address this need a de novo asymmetric synthetic approach to oligosaccharides was developed; where the carbons and asymmetry of the sugar are derived from chiral furan alcohols. To enable this approach highly practical and enantioselective approach to chiral furan alcohols from inexpensive achiral starting materials is required. Herein we will present our latest efforts at the synthesis of substituted furan alcohols from 2-acetyl furan and its application to the synthesis of C-6 substituted D-/L-sugars.