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Enantiomeric synthesis of l- (or 1S,2R,3S,5S)-bicarbocyclic[3.1.0] nucleosides

✍ Scribed by Luigi A. Agrofoglio; Christine Demaison; Loïc Toupet

Book ID: 104209472
Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 480 KB
Volume: 55
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(99)00424-x

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✦ Synopsis

The total synthesis of L-(or IS,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 (IS,2R,3S,5S)-2-(3aminobicyclo[3.1.0]bex-2-yl)ethanol ( 7).

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