
%0 Journal Article
%A Hughes, AB 
%A Stick, RV 
%A Tilbrook, DMG 
%T The Synthesis of Some Carbohydrate-Derived Precursors to Tylonolide, the Aglycon of the Antibiotic Tylosin
%J Australian Journal of Chemistry
%D 1990/10/01
%V 43
%N 10
%P 1681-1695
%K 
%R https://doi.org/10.1071/CH9901681
%U https://www.publish.csiro.au/paper/CH9901681 
%X Treatment of methyl 2,3-anhydro-4,6-O-benzylidene-&#945;-D-alloside with the anion derived from trimethyl(prop-1-ynyl)silane, allylmagnesium chloride or isobutenylmagnesium chloride introduces a three- or four- carbon substituent at C2 of the sugar. In each case, a hydroboration-oxidation sequence helps convert the centre of unsaturation in the new substituent into a carboxylic acid residue. Subsequent manipulations allow the introduction ofanother carbon at C6 of the sugar to give a highly functionalized precursor to the C1-C9 fragment of tylonolide, the aglycon of the antibiotic tylosin. Attempts at the introduction of an axial methyl group at C4 of the extended sugar also described. 
