Asymmetric synthesis of the cytotoxic lactone (+)-cardiobutanolide and two novel analogues. Issue 9 (28th February 2019)

• Record Type: Journal Article
• Authors: Kovačević, Ivana; Popsavin, Mirjana; Rodić, Marko V.; Kojić, Vesna; Popsavin, Velimir
• Is Part Of: Tetrahedron letters. Volume 60:Issue 9(2019)
• Page Start: 684
• Page End: 687
• Publication Date: 2019-02-28
• Subjects: Cardiobutanolide -- Analogues -- Styryl lactones -- Antitumour agents -- Asymmetric synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.01.059
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A new total synthesis of cardiobutanolide and two new analogues has been completed. In vitro antitumour activity of this natural product and analogues was recorded. (+)-Cardiobutanolide was identified as the most active compound. Abstract: A new asymmetric synthesis of the naturally occurring styryl lactone cardiobutanolide and two novel analogues have been achieved starting fromd -xylose. The key steps of the synthesis included an initial zinc mediated reductive THF-ring opening, stereoselective olefination and Sharpless asymmetric dihydroxylation. It was shown that cardiobutanolide (1 ) exhibits promising in vitro antitumour properties against certain human neoplastic cell lines. It was more potent than the commercial anticancer agent doxorubicin against three cell lines (K562, HL-60 and Raji).