Projects per year
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.
Original language | English |
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Pages (from-to) | 810-814 |
Number of pages | 5 |
Journal | Nature Chemistry |
Volume | 6 |
Issue number | 9 |
Early online date | 27 Jul 2014 |
DOIs | |
Publication status | Published - 1 Sep 2014 |
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Dive into the research topics of 'Synthesis of hydroxyphthioceranic acid using a traceless lithiation-borylation-protodeboronation strategy'. Together they form a unique fingerprint.Projects
- 2 Finished
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Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis
14/05/12 → 13/01/18
Project: Research
Profiles
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Professor Varinder K Aggarwal
- School of Chemistry - Alfred Capper Pass Chair of Chemistry
- Synthesis
- Supramolecular and Mechanistic Chemistry
- Catalysis
Person: Academic , Member