Journal
SYNLETT
Volume -, Issue 14, Pages 2509-2512Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-2004-834810
Keywords
fluorine. antitumor agent; asymmetric synthesis; camptothecin; topoisomerase I
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20-Deoxy-20-fluorocamptothecin (2) has been synthesized as an isosteric analogue of camptothecin (1). The use of selectfluor or N-fluorobenzenesulfonimide for the electrophilic fluorination of 20-deoxycamptothecin (3) yields the target compound. Enantioselective fluorination of 3 was also achieved using our previously described cinchona alkaloids/selectfluor combination to provide both enantiomers of 2 with 88% ee and 81% ee, respectively.
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