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Synthesis 2005(7): 1157-1163
DOI: 10.1055/s-2005-861861
DOI: 10.1055/s-2005-861861
PAPER
© Georg Thieme Verlag Stuttgart · New York
Fluorination of Betulinines and Other Triterpenoids with DAST
Weitere Informationen
Received
1 September 2004
Publikationsdatum:
10. März 2005 (online)
Publikationsverlauf
Publikationsdatum:
10. März 2005 (online)
Abstract
Betulinines are lupane, des-E-lupane, 18-lupene, 20(29)-lupene and 18α-oleanane derivatives with antitumor activity. We examined fluorination of these derivatives using diethylaminosulfur trifluoride (DAST) as fluorinating agent. We prepared 19β,28-epoxy-2,2-difluoro-18α-oleanan-3-one (3c), 19β,28-epoxy-2,2-difluoro-18α-oleanan-3β-ol (4a), methyl 3β-acetoxy-30-fluorolup-20(29)-ene-28-oate (6b), 3β,28-diacetoxy-22-oxo-21,21-difluorolup-18-ene (8b) and several other fluorinated betulinines for in vitro cytotoxicity tests which failed to demonstrate significant anticancer activity so far.
Key words
antitumor agents - fluorine - rearrangements - steric hindrance - terpenoids
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