Tetrahedron Letters p. 3443 - 3446 (1998)
Update date:2022-08-03
Topics:
Hong, Joon H.
Lee, Kyeong
Choi, Yongseok
Chu, Chung K.
Enantiomeric synthesis of 3′-fluoro-apionucleosides was accomplished from 1,2-O-isopropylidene D-glyceraldehyde. The key intermediate, γ,δ-unsaturated tert-fluoro ethyl ester 7 from the fluoro allylic alcohol derivative 5 was achieved via Claisen rearrangement reaction with a 90.4% enantioselectivity. The condensation of the intermediate 10 with silylated N4-benzoylcytosine and 6-chloropurine followed by deprotection gave the desired pyrimidine and purine apionucleosides, respectively.
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Doi:10.1039/J19680002149
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(2011)