(+)-Neplanocin F, 2′-fluoroneplanocin, and a 6′-isoneplanocin via a common versatile cyclopentenol precursor

Reductive (diisobutylaluminum hydride) ring opening of an acetal protected cyclopentenol has provided a precursor adaptable to uniquely substituted carbocyclic nucleosides. To illustrate the broad implication of this process the preparation of unnatural (+)-neplanocin F, an ara-like 2′-fluoroneplanocin, and a 6′- isomeric l-like neplanocin analog is described.