%0 Journal Article
%T Synthesis of Biotinylated Galiellalactone Analogues
%A Zilma Escobar
%A Martin Johansson
%A Anders Bjartell
%A Rebecka Hellsten
%A Olov Sterner
%J International Journal of Organic Chemistry
%P 225-235
%@ 2161-4695
%D 2014
%I Scientific Research Publishing
%R 10.4236/ijoc.2014.44026
%X Two biotinylated derivatives
of the fungal metabolite galiellalactone (1) were synthesized in order to facilitate
the investigation of the molecular mechanism of action of the<span> </span>galiellalactonoids. Galiellalactone is a STAT3-signaling inhibitor that
inhibits growth <i>in vitro</i> as well as <i>in vivo</i> of prostate cancer cells expressing
activated STAT3. To provide a suitable point of attachment for biotin, the 8-hydroxymethyl
derivative (3) and its 7-phenyl analogue 4 were synthesized by a modified tandem
Pd-catalysed carbonylation and intramolecular vinyl allene Diels-Alder procedure
previously developed. The two primary alcohols obtained, 3 and 4, were coupled to
biotin as the 6-aminohexanoic acid amide, activated as the acid chloride, yielding
the derivatives 5 and 6.
%K STAT3
%K Galiellalactone
%K Biotin
%K Synthesis
%U http://www.scirp.org/journal/PaperInformation.aspx?PaperID=51465