Stereoselective total synthesis of all the stereoisomers of (+)- and (−)-febrifugine and halofuginone

[Display omitted] •An expeditious total synthesis of all the stereoisomers of Febrifugine is achieved.•An expeditious total synthesis of all the stereoisomers of Halofuginone is achieved.•Commercially inexpensive carbohydrates were used as chiral starting materials.•Wacker oxidation was used as the...

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Bibliographic Details
Published in:Tetrahedron letters 2020-07, Vol.61 (30), p.152151, Article 152151
Main Authors: Perali, Ramu Sridhar, Bandi, Anjaneyulu
Format: Article
Language:English
Subjects:
Carbohydrates
Glycals
Natural products
Stereoselective
Total synthesis
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Summary:[Display omitted] •An expeditious total synthesis of all the stereoisomers of Febrifugine is achieved.•An expeditious total synthesis of all the stereoisomers of Halofuginone is achieved.•Commercially inexpensive carbohydrates were used as chiral starting materials.•Wacker oxidation was used as the key step in generating the key intermediate. A convenient method for the total synthesis of all the stereoisomers of febrifugine and halofuginone using D-arabinose and L-arabinose as the key starting materials is reported. Apart from the inherent stereocenters in these pentose sugars, the method utilizes the selective hydrogenolysis of the anomeric O-benzyl group, stereoselective Grignard reaction and Wacker oxidation as the key steps to obtain the important precursors for the total synthesis.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.152151