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Synthesis 1994; 1994(12): 1476-1484
DOI: 10.1055/s-1994-25717
DOI: 10.1055/s-1994-25717
feature article
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
A Novel Route to Pyrimidine Nucleosides via Intramolecular Couplings of Bases with 2′-Deoxyribosides: Quick and Stereospecific...but with a 'Twist'
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Publikationsverlauf
Publikationsdatum:
25. April 2002 (online)
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Coupling of a pyrimidine base (e.g., thymine) with the C-5′ hydroxyl group of a 2′-deoxyriboside via bromoetherification leads to intermediates which can be converted to cyclonucleosides under the influence of Lewis acids. Ring opening by β-elimination affords nucleosides which are stereopure at the required anomeric position.