Tetrahedron

2-Aza-3-oxabicyclo [2.2. 1] heptene hydrochloride: An exceptionally versatile synthon for carbocyclic sugars and nucleosides

S Ranganathan, KS George

Index: Ranganathan, Subramania; George, K. Shaji Tetrahedron, 1997 , vol. 53, # 9 p. 3347 - 3362

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Citation Number: 21

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 ...