Tetrahedron p. 3347 - 3362 (1997)
Update date:2022-08-04
Topics:
Ranganathan, Subramania
George, K. Shaji
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 functionalization, 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.
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