%0 Journal Article
%T A formal synthesis of (+)-muricatacin from D-xylose
%A VELIMIR POPSAVIN
%A SANJA GRABEZ
%A IVANA KRSTIC
%A MIRJANA POPSAVIN
%J Journal of the Serbian Chemical Society
%D 2003
%I Serbian Chemical Society
%X A multistep route towards the aldehydo-lactone 19, the final chiral precursor in a new stereospecific synthesis of (+)-muricatacin, has been developed starting from D-xylose. The key step of the synthesis involves an E-selective Wittig olefination of the lactol 6 with methoxycarbonylmethylidene triphenylphosphorane, followed by successive catalytic reduction and g-lactonisation processes. Subsequent selective functional groups interconversions furnished the key six-carbon intermediate 19, which can be converted into the (+)-muricatacin via a three-step sequence already described in the chemical literature.
%K muricatacin
%K Wittig reaction
%K g-lactone
%K stereospecific synthesis
%K D-xylose
%U http://www.shd.org.yu/HtDocs/SHD/Vol68/No11/V68-No11-02.pdf