Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid
Authors:
- 18 June 2015
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition
- Vol. 54 (32) , 9319-9322
Abstract
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 sp3–sp3 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.Keywords
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