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Facile Synthesis of Enantiomerically Pure Carbafuranoses: Precursors of Carbocyclic Nucleosides
Author(s) -
Gallos John K.,
Dellios Constantinos C.,
Spata Ekaterini E.
Publication year - 2001
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 - 10.1002/1099-0690(200101)2001:1<79::aid-ejoc79>3.0.co;2-1
Subject(s) - chemistry , organic chemistry , stereochemistry , combinatorial chemistry
An efficient and highly diastereoselective synthetic approach to enantiomerically pure (−)‐(1 R ,2 R ,3 S ,4 R )‐ and (+)‐(1 S ,2 S ,3 R ,4 S )‐4‐hydroxyethylcyclopentane‐1,2,3‐triols is reported, which involves conversion of D ‐ribose or D ‐arabinose to (+)‐ or (−)‐ethyl Z ‐4,5‐isopropylidenedioxyhepta‐2,6‐dienoate, mercuration of the terminal double bond by mercury(II) acetate, followed by reductive radical cyclization and further standard reduction and deprotection manipulations.