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Convergent Synthesis of Digitoxin: Stereoselective Synthesis and Glycosylation of the Digoxin Trisaccharide Glycal
Author(s) -
McDonald Frank E.,
Reddy K. Subba
Publication year - 2001
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 - 10.1002/1521-3773(20011001)40:19<3653::aid-anie3653>3.0.co;2-w
Subject(s) - digitoxin , stereoselectivity , glycosylation , trisaccharide , chemistry , digoxin , glycal , combinatorial chemistry , stereochemistry , convergent synthesis , catalysis , organic chemistry , biochemistry , heart failure , medicine
Tungsten‐catalyzed alkynol cycloisomerization and iterative acid‐catalyzed stereoselective glycosylations form the basis of a revolutionary new strategy for oligosaccharide synthesis. The method has been successfully applied to a highly convergent synthesis of Digitalis 2‐deoxyglycosides (see scheme).