Total Synthesis of L-Allose, L-Talose, and Derivatives

Article abstract of DOI:10.1002/hlca.19890720212

(1S,4R,5S,6S)-5-exo,6-exo-(Isopropylidenedioxy)-7-oxabicyclo<2.2.1>heptan-2-one ((-)-1) was transformed with high stereoselectivity to L-allose.Similarly, enantiomer (+)-1 was transformed into L-talose.The ketones (+)-1 and (-)-1 were derived from furan and 1-cyanovinyl (1S)-camphanate and 1-cyanovinyl (1R)-camphanate, respectively.