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Polyol Synthesis through Hydrocarbon Oxidation: De Novo Synthesis of L ‐Galactose
Author(s) -
Covell Dustin J.,
Vermeulen Nicolaas A.,
Labenz Nathan A.,
White M. Christina
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200603321
Subject(s) - polyol , chemistry , hydrocarbon , galactose , stereochemistry , organic chemistry , polyurethane
Carbohydrates from hydrocarbons : A hydrocarbon oxidation strategy for the synthesis of chiral polyols is validated by the enantioselective, de novo synthesis of differentially protected L ‐galactose (see scheme, TBS= tert ‐butyldimethylsilyl, Bn=benzyl). Key to this strategy is the selective CH oxidation method for transforming protected chiral allylic alcohols into ( E )‐2‐butene‐1,4‐diol derivatives.
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