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Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid
Author(s) -
Xu Shiqing,
Oda Akimichi,
Bobinski Thomas,
Li Haijun,
Matsueda Yohei,
Negishi Eiichi
Publication year - 2015
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.201503818
Subject(s) - enantioselective synthesis , chemistry , convergent synthesis , stereoselectivity , combinatorial chemistry , catalysis , stereochemistry , stereoisomerism , organic chemistry
A new strategy for highly concise, convergent, and enantioselective access to polydeoxypropionates has been developed. ZACA‐Pd‐catalyzed vinylation was used to prepare smaller deoxypropionate fragments, and then two key sequential Cu‐catalyzed stereocontrolled sp 3 –sp 3 cross‐coupling reactions allowed convergent assembly of smaller building blocks to build‐up long polydeoxypropionate chains with excellent stereoselectivity. We employed this strategy for the synthesis of phthioceranic acid, a key constituent of the cell‐wall lipid of Mycobacterium tuberculosis, in just 8 longest linear steps with full stereocontrol.