Total synthesis and biological activity of the proposed structure of phaeosphaeride A

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  • Anthoula Chatzimpaloglou - , Aristotle University of Thessaloniki (Author)
  • Maria P. Yavropoulou - , Leiden University (Author)
  • Karien E. Rooij - , Leiden University (Author)
  • Ralf Biedermann - , TUD Dresden University of Technology (Author)
  • Uwe Mueller - , Helmholtz Centre Berlin for Materials and Energy (Author)
  • Stefan Kaskel - , Chair of Inorganic Chemistry I (Author)
  • Vasiliki Sarli - , Aristotle University of Thessaloniki (Author)


The total synthesis of the structure assigned to the natural product phaeosphaeride A 1a was accomplished. The key steps involve the addition of vinyllithium reagent 7 to the acetonide-protected aldehyde 8 to access the carbon backbone of 1a, the introduction of the methoxylamino group followed by intramolecular hetero-Michael cyclization, and methanol elimination to form the dihydropyran ring. In this study, both enantiomers of 1a were synthesized and tested for biological activity. Preliminary results showed that (6R,7R,8R)-1a and (6S,7S,8S)-1a inhibit STAT3-dependent transcriptional activity in a dose-dependent manner and exhibit antiproliferative properties in breast (MDA-MB-231) and pancreatic (PANC-1) cancer cells.


Original languageEnglish
Pages (from-to)9659-9667
Number of pages9
JournalJournal of organic chemistry
Issue number21
Publication statusPublished - 2 Nov 2012

External IDs

PubMed 23050677


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