
%0 Journal Article
%A Burns,, Christopher J. 
%A Gill, Melvyn 
%A Saubern, Simon 
%T Pigments of Fungi. XLIV Synthesis of Differentially Protected Chiral Pentane-1,3,5-triol Derivatives; Confirmation of the Absolute Configuration of Naturally Occurring 3-Acetoxy-2,3-dihydropiptoporic Acid
%J Australian Journal of Chemistry
%D 1998/01/13
%V 50
%N 11
%P 1067-1080
%K 
%R https://doi.org/10.1071/C97111
%U https://www.publish.csiro.au/paper/C97111 
%X (R)-1-t-Butyldimethylsilyloxy-5-phenylmethoxypentan-3-ol (25), prepared in 68% yield and &#62;99&#183;9% enantiomeric excess over six steps from commercially available but-3-yn-1-ol by Katsuki-Sharpless epoxidation, was converted by way of its 3-methoxymethyl ether (30) into both enantiomers (6) and (11) of methyl 3,5-diacetoxypentanoate. Direct comparison of these substances with the ester derived by oxidative degradation of the fungus pigment 3-acetoxy-2,3-dihydropiptoporic acid (1) confirmed the (R) absolute configuration of the natural product. Some new chemistry of the differentially protected chiral triols (12) and (30) is described. 
