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Asymmetric Synthesis of (-)-6'-β-Fluoro-aristeromycin via Stereoselective Electrophilic Fluorination.
- Source :
-
Organic Letters . 11/3/2017, Vol. 19 Issue 21, p5732-5735. 4p. - Publication Year :
- 2017
-
Abstract
- (-)-6'-β-Fluoro-aristeromycin (2), a potent inhibitor of S-adenosylhomocysteine (AdoHcy) hydrolase, has been synthesized via stereoselective electrophilic fluorination followed by a purine base build-up approach. Interestingly, purine base condensation using a cyclic sulfate resulted in a synthesis of (+)-5'-β-fluoro-isoaristeromycin (2a). Computational analysis indicates that the fluorine atom controlled the regioselectivity of the purine base substitution. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 15237060
- Volume :
- 19
- Issue :
- 21
- Database :
- Academic Search Index
- Journal :
- Organic Letters
- Publication Type :
- Academic Journal
- Accession number :
- 126093305
- Full Text :
- https://doi.org/10.1021/acs.orglett.7b02470