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Synthesis of hydroxyphthioceranic acid using a traceless lithiation–borylation–protodeboronation strategy
| Content Provider | Semantic Scholar |
|---|---|
| Author | Rasappan, Ramesh Aggarwal, Varinder K. |
| Copyright Year | 2014 |
| Abstract | 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. Coupling of carbamates with boronic esters followed by protodeboronation creates a new carbon–carbon bond, leaving behind no trace of the functional groups used to create it. Now, methodology for the protodeboronation of alkyl pinacol boronic esters has been developed and an iterative lithiation–borylation–protodeboronation strategy used in a 14-step stereocontrolled synthesis of hydroxyphthioceranic acid. |
| Starting Page | 810 |
| Ending Page | 814 |
| Page Count | 5 |
| File Format | PDF HTM / HTML |
| DOI | 10.1038/nchem.2010 |
| PubMed reference number | 25143217 |
| Journal | Medline |
| Volume Number | 6 |
| Alternate Webpage(s) | http://www.chm.bris.ac.uk/org/aggarwal/docs/publications/227pub.pdf |
| Alternate Webpage(s) | https://doi.org/10.1038/nchem.2010 |
| Journal | Nature Chemistry |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
