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Synthesis of the 5′‐Fluoro‐2′β‐methyl Analogues of Neplanocin
Author(s) -
Kumamoto Hiroki,
Kobayashi Marina,
Kato Nobuyuki,
Balzarini Jan,
Tanaka Hiromichi
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100062
Subject(s) - chemistry , intramolecular force , cyclopentenone , stereochemistry , stereoselectivity , ring closing metathesis , metathesis , selectfluor , electrophile , double bond , electrophilic fluorination , ring (chemistry) , methyl group , fluorine , organic chemistry , group (periodic table) , polymer , polymerization , catalysis
Synthesis 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