Ranganathan, Subramania ; Shaji George, K. (1997) 2-Aza-3-oxabicyclo[2.2.1]heptene hydrochloride: an exceptionally versatile synthon for carbocyclic sugars and nucleosides Tetrahedron, 53 (9). pp. 3347-3362. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/S0040-4020(97)00057-4
Abstract
The transformation of cyclopentadiene to 5'-desmethylene 1'-aza carbocyclic sugars has been achieved in four steps: 1. Cycloaddition of chloronitrosocyclohexane to 2-aza-3-oxabicyclo[2.2.1]heptene hydrochloride in EtOH-Et2O, 2. Nitrogen functiona-lization, 3. cis hydroxylation and 4. N---O bond cleavage. The protocols provided enable practical access to a range of 5'-desmethylene carbocyclic sugar analogs whose utility has been illustrated with synthesis of a novel 5'-desmethylene analog of aristeromycin.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 48874 |
| Deposited On: | 20 Jul 2011 06:50 |
| Last Modified: | 20 Jul 2011 06:50 |
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