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Three‐Step Synthesis of Sialic Acids and Derivatives
Author(s) -
Hong Zhangyong,
Liu Lei,
Hsu CheChang,
Wong ChiHuey
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.200601555
Subject(s) - cycloaddition , construct (python library) , sialic acid , ring (chemistry) , nitrone , chemistry , base (topology) , combinatorial chemistry , stereochemistry , computer science , organic chemistry , biochemistry , catalysis , programming language , mathematics , mathematical analysis
Flexible yet efficient : Sialic acids such as L ‐ N ‐acetylneuraminic acid (see picture) can be synthesized in only three steps by 1) vinylation of an aldose through a modified Petasis coupling reaction, 2) 1,3‐dipolar cycloaddition with a nitrone to construct an isoxazolidine ring, and 3) base‐catalyzed β elimination/ring opening of the isoxazolidine to generate a γ‐hydroxy‐α‐keto acid.
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