Synthesis of the 5′‐Fluoro‐2′β‐methyl Analogues of Neplanocin

Abstract

AbstractSynthesis of the 5′‐fluoro‐2′‐β‐methyl analogues of neplanocin was carried out. Key intermediate cyclopentenone 19 was prepared from methyl α‐D‐mannopyranoside by a new approach consisting of ring‐closing metathesis, stereoselective introduction of the 2′‐methyl group, and intramolecular oxyselenenylation of the double bond as representative steps. Subsequent introduction of a fluorine atom at the 5′‐position of 19 was performed by electrophilic fluorination by using Selectfluor