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Total Synthesis of Sialic Acid by a Sequential Rhodium‐Catalyzed Aziridination and Barbier Allylation of D ‐Glycal
Author(s) -
Lorpitthaya Rujee,
Suryawanshi Sharad B.,
Wang Siming,
Pasunooti Kalyan Kumar,
Cai Shuting,
Ma Jimei,
Liu XueWei
Publication year - 2011
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.201104516
Subject(s) - rhodium , glycal , sialic acid , chemistry , stereoselectivity , catalysis , nucleophile , n acetylneuraminic acid , organic chemistry , biochemistry
Acid test : Sialic acid Neu5Ac was synthesized in a regio and stereoselective manner from a glycal (see scheme) via a [1,2,3]‐oxathiazocane‐2,2‐dioxide intermediate. The sequential rhodium‐catalyzed aziridination/indium‐mediated Barbier allylation approach adopted offers a potentially flexible route to other sialic acid derivatives, since the oxathiazocane intermediate was compatible with a variety of nucleophiles.