New and Efficient Synthesis of 6-Deoxy-L-gulose

Article abstract of DOI:10.1021/jo01290a001

An efficient synthetic procedure for the transformation of D-glucurono-γ-lactone to 6-deoxy-L-gulose (20) in five steps and 52 percent yield is described.The scheme relies on the selective blocking of the 2-(silyl ether) and 3,5-(isopropylidene) hydroxyl groups and then diisobutylaluminum hydride reduction of the lactone carbonyl.An alternate route that relies on the more standard sodium amalgam reduction of the lactone triol was found to be technically inefficient and to result in a poor overall yield.