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http://dx.doi.org/10.1021/op0602371

has been cited by the following article:

• TITLE: Synthesis of Biotinylated Galiellalactone Analogues

  AUTHORS: Zilma Escobar, Martin Johansson, Anders Bjartell, Rebecka Hellsten, Olov Sterner

  KEYWORDS: STAT3, Galiellalactone, Biotin, Synthesis

  JOURNAL NAME: International Journal of Organic Chemistry, Vol.4 No.4, November 18, 2014

  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.