期刊
NATURE CHEMISTRY
卷 6, 期 9, 页码 810-814出版社
NATURE PUBLISHING GROUP
DOI: 10.1038/NCHEM.2010
关键词
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资金
- Engineering and Physical Science Research Council [EP/I038071/1]
- European Research Council (FP7) [246785]
- Marie Curie Fellowship program (EC FP7) [329578]
- EPSRC [EP/I038071/1, EP/K03927X/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/K03927X/1, EP/I038071/1] Funding Source: researchfish
In planning organic syntheses, disconnections are most often made adjacent to functional groups, which assist in C-C bond formation. For molecules devoid of obvious functional groups this approach presents a problem, and so functionalities must be installed temporarily and then removed. Here we present a traceless strategy for organic synthesis that uses a boronic ester as such a group in a one-pot lithiation-borylation-protodeboronation sequence. To realize this strategy, we developed a methodology for the protodeboronation of alkyl pinacol boronic esters that involves the formation of a boronate complex with a nucleophile followed by oxidation with Mn(OAc)(3) in the presence of the hydrogen-atom donor 4-tert-butylcatechol. Iterative lithiation-borylation-protodeboronation allows the coupling of smaller fragments to build-up long alkyl chains. We employed this strategy in the synthesis of hydroxyphthioceranic acid, a key component of the cell-wall lipid of the virulent Mycobacterium tuberculosis, in just 14 steps (longest linear sequence) with full stereocontrol.
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