Subscribe to RSS
DOI: 10.1055/s-0030-1257880
Synthesis of R207910
Contributor(s):Philip KocienskiThe University of Tokyo, Japan
Catalytic Asymmetric Synthesis of R207910
J. Am. Chem. Soc. 2010, 132: 7905-7907
Publication History
Publication Date:
23 August 2010 (online)
Key words
R207910 - catalytic enantioselective proton migration - allylation - ytterbium(III) hexamethyl-disilazide - copper(I) fluoride
Significance
R207910 is a selective inhibitor of the ATP synthase proton pump of both drug-sensitive and drug-resistant Mycobacterium tuberculosis. The synthesis of R207910 depicted features two novel transformations: (1) a catalytic enantioselective proton migration using a bimetallic Y complex (A → C) and (2) a CuF-catalyzed diastereoselective allylation reaction (C → E).
Comment
Mass spectrometric evidence suggests that the active catalyst in the enantioselective proton migration reaction (A → C) is a ternary complex comprising two ytterbium atoms, three molecules of the ligand B and one molecule of 4-methoxypyridine N-oxide. A catalytic cycle for the reaction is postulated. The allylation step could be performed with as little as 1 mol% of the CuF complex at the expense of a diminished dr (5.6:1).