Tetrahedron p. 8075 - 8082 (1999)
Update date:2022-08-17
Topics:
Agrofoglio, Luigi A.
Demaison, Christine
Toupet, Loic
The total synthesis of L- (or 1S,2R,3S,5S)-bicarbocyclic nucleosides (8- 15) has been accomplished. The key intermediate 3 was synthesized in two steps from the known chiral compound 1 through a stereoselective cyclopropanation under Furukawa conditions and its X-ray structure has been determined. The derivative 4 was utilized to obtain thymine derivative (8). Amino exocyclic pyrimidine (9-12) and purine (13-15) bicarbocyclic L- nucleosides were obtained from the (1S,2R,3S,5S)-2-(3- aminobicyclo[3.1.0]hex-2-yl)ethanol (7).
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