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Asymmetric synthesis of the cytotoxic lactone (+)-cardiobutanolide and two novel analogues |
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| Authors: | Ivana Kovačević Mirjana Popsavin Marko V. Rodić Vesna Kojić Velimir Popsavin |
| Affiliation: | 1. Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovi?a 3, 21000 Novi Sad, Serbia;2. Oncology Institute of Vojvodina, Put Dr Goldmana 4, 21204 Sremska Kamenica, Serbia;3. Serbian Academy of Sciences and Arts, Knez Mihajlova 35, 11000 Belgrade, Serbia |
| Abstract: | A new asymmetric synthesis of the naturally occurring styryl lactone cardiobutanolide and two novel analogues have been achieved starting from d-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). |
| Keywords: | Cardiobutanolide Analogues Styryl lactones Antitumour agents Asymmetric synthesis |
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