
TY  - JOUR
A1  - Burns,, Christopher J. 
A1  - Gill, Melvyn 
A1  - Saubern, Simon 
T1  - 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
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1998
VL  - 50
IS  - 11
SP  - 1067
EP  - 1080
KW  - 
UR  - https://doi.org/10.1071/C97111 
N2  - (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. 
ER  -

