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

Publikation: Beitrag in FachzeitschriftForschungsartikelBeigetragenBegutachtung

Beitragende

  • Anthoula Chatzimpaloglou - , Aristotle University of Thessaloniki (Autor:in)
  • Maria P. Yavropoulou - , Leiden University (Autor:in)
  • Karien E. Rooij - , Leiden University (Autor:in)
  • Ralf Biedermann - , Technische Universität Dresden (Autor:in)
  • Uwe Mueller - , Helmholtz-Zentrum Berlin für Materialien und Energie (HZB) (Autor:in)
  • Stefan Kaskel - , Professur für Anorganische Chemie (I) (AC1) (Autor:in)
  • Vasiliki Sarli - , Aristotle University of Thessaloniki (Autor:in)

Abstract

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.

Details

OriginalspracheEnglisch
Seiten (von - bis)9659-9667
Seitenumfang9
FachzeitschriftJournal of organic chemistry
Jahrgang77
Ausgabenummer21
PublikationsstatusVeröffentlicht - 2 Nov. 2012
Peer-Review-StatusJa

Externe IDs

PubMed 23050677

Schlagworte

Ziele für nachhaltige Entwicklung

ASJC Scopus Sachgebiete

Bibliotheksschlagworte