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A Convergent and Stereoselective Synthesis of the Glycolipid Components Phthioceranic Acid and Hydroxyphthioceranic Acid
Author(s) -
Pischl Matthias C.,
Weise Christian F.,
Müller MarcAndré,
Pfaltz Andreas,
Schneider Christoph
Publication year - 2013
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.201303776
Subject(s) - stereoselectivity , iridium , glycolipid , methylation , convergent synthesis , chemistry , coupling reaction , stereochemistry , catalysis , combinatorial chemistry , organic chemistry , biochemistry , gene
Simply convergent : The polydeoxypropionates 1 and 2 are important constituents of the cell wall of Mycobacterium tuberculosis. Key steps in their total synthesis include two Suzuki–Miyaura cross‐coupling reactions and two highly diastereoselective iridium‐catalyzed hydrogenations. The trideoxypropionates employed as central building blocks were prepared by sequential oxy‐Cope rearrangement, hydrogenation, and enolate methylation.