De novo synthesis of L-colitose and L-rhodinose building blocks.

A divergent, practical, and efficient de novo synthesis of fully functionalized L-colitose (3,6-dideoxy-L-galactose), 2-epi-colitose (3,6-dideoxy-L-talose), and L-rhodinose (2,3,6-trideoxy-L-galactose) building blocks has been achieved using inexpensive, commercially available (S)-ethyl lactate as the starting material. The routes center around a diastereoselective Cram-chelated allylation that provides a common homoallylic alcohol intermediate. Oxidation of this common intermediate finally resulted in the synthesis of the three monosaccharide building blocks.