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A Convergent and Stereoselective Synthesis of the Glycolipid Components Phthioceranic Acid and Hydroxyphthioceranic Acid


  • This work was supported by the Deutsche Forschungsgemeinschaft (SCHN 441/6-2) and the Studienstiftung des Deutschen Volkes (PhD fellowship to C.F.W.). We gratefully acknowledge generous donations of chemicals from BASF, Evonik, and Chemetall and thank Dr. Peter Lönnecke for the X-ray crystal analysis and Johannes Diesel (both University of Leipzig) for the synthesis of precursors.


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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.

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