Total Synthesis of Sialic Acid by a Sequential Rhodium‐Catalyzed Aziridination and Barbier Allylation of  D ‐Glycal | Zendy

Lorpitthaya Rujee | Zendy; Suryawanshi Sharad B. | Zendy; Wang Siming | Zendy; Pasunooti Kalyan Kumar | Zendy; Cai Shuting | Zendy; Ma Jimei | Zendy; Liu XueWei | Zendy

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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.

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