title: De novo synthesis of L-colitose and L-rhodinose building blocks.
abstract: 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.
authors.affiliation: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany.
authors.forename: Oliviana
authors.initials: O
authors.lastname: Calin
authors.forename: Rajan
authors.initials: R
authors.lastname: Pragani
authors.forename: Peter H
authors.initials: PH
authors.lastname: Seeberger
mesh_terms: D060326:Chemistry Techniques, Synthetic; D003837:Deoxy Sugars / Q000138:chemical synthesis*; D009005:Monosaccharides / Q000138:chemical synthesis*
chemical_list: D003837:Deoxy Sugars; D009005:Monosaccharides; C438054:rhodinose; C025141:colitose