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 IJOC  Vol.4 No.4 , December 2014
Synthesis of Biotinylated Galiellalactone Analogues
Abstract: 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 galiellalactonoids. Galiellalactone is a STAT3-signaling inhibitor that inhibits growth in vitro as well as in vivo 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.
Cite this paper: Escobar, Z. , Johansson, M. , Bjartell, A. , Hellsten, R. and Sterner, O. (2014) Synthesis of Biotinylated Galiellalactone Analogues. International Journal of Organic Chemistry, 4, 225-235. doi: 10.4236/ijoc.2014.44026.
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