1403681-33-3Relevant academic research and scientific papers
Total synthesis and biological activity of the proposed structure of phaeosphaeride A
Chatzimpaloglou, Anthoula,Yavropoulou, Maria P.,Rooij, Karien E.,Biedermann, Ralf,Mueller, Uwe,Kaskel, Stefan,Sarli, Vasiliki
, p. 9659 - 9667 (2013/01/15)
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.
