
%0 Journal Article
%A Engelhardt, LM 
%A Skelton, BW 
%A Stick, RV 
%A Tilbrook, DMG 
%A White, AH 
%T Approaches to the Synthesis of Lincosamine, a Derived Portion of the Antibiotic Lincomycin
%J Australian Journal of Chemistry
%D 1990/10/01
%V 43
%N 10
%P 1657-1680
%K 
%R https://doi.org/10.1071/CH9901657
%U https://www.publish.csiro.au/paper/CH9901657 
%X A variety of approaches towards the synthesis of lincosamine, a derived portion of the antibiotic lincomycin , are reported. Initial approaches involved the intramolecular delivery of a nitrogen atom ( trichloroacetimidate , trichloroacetylcarbamate , carbamate, 2-amino-2- phenylacetate ) attached to O4 onto C6 of a 6,7-anhydrooctoside. Later approaches, albeit more direct but again largely unsuccessful, involved the Sharpless titanium(IV)-mediated nucleophilic opening of a suitable 6,7-anhydrooctose, and the Sharpless oxyamination and the aziridination of suitable octenoses . As an aid to the structure elucidation of several compounds encountered in this work, single-crystal X-ray structure determinations are reported for methyl 6,7-anhydro-2,3-di-O-benzyl-8-deoxy-&#945;-D-threo-D-galacto-octopyranoside , methyl 6,7-anhydro-2,3-di-O-benzyl-8-deoxy-&#945;-D-threo-D-gluco-octopyranoside and 7-azido-7-deoxy-1,2:3,4-di-O-isopropylidene-&#946;-L-erythro-Dgalacto-octose. 
