
TY  - JOUR
A1  - Elsworth, Catherine 
A1  - Gill, Melvyn 
A1  - Raudies, Evelin 
A1  - Ten, Abilio 
T1  - Pigments of Fungi. LXIII. Synthesis of (1<emph type="2">S</emph>,3<emph type="2">R</emph>)- and (1<emph type="2">R</emph>,3<emph type="2">S</emph>)-Austrocortilutein and the Enantiomeric Purity of Austrocortilutein in some Australian <emph type="2">Dermocybe</emph> Toadstools
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2000
VL  - 53
IS  - 1
SP  - 41
EP  - 46
KW  - Fungi; pigments; toadstools; quinones; Australian; Dermocybe; cycloaddition.
UR  - https://doi.org/10.1071/CH99144 
N2  - The naturally occurring tetrahydroanthraquinones (1S,3R)- and (1R,3S)-austrocortilutein (1b) and (1d), respectively, are synthesized for the first time in enantiomerically pure form by Diels&#8211;Alder cycloaddition between the functionalized butadiene derivative (4) and the corresponding monochiral trans-1,3-dihydroxy-1,2,3,4- tetrahydro-5,8-naphthoquinone (5a) or (5b), themselves derived from citramalic acid. Separation of the four stereoisomeric austrocortiluteins by using h.p.l.c. over a chiral stationary phase reveals that the enantiomeric purity of the (1S,3S)- and (1R,3R)-quinones (1a) and (1c) varies from species to species whereas the (1S,3R)-isomer (1b) is, in the five cases examined, enantiomerically pure. 
ER  -

