Synthesis of hydroxyphthioceranic acid using a traceless lithiation-borylation-protodeboronation strategy

Ramesh Rasappan, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

60 Citations (Scopus)

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 languageEnglish
Pages (from-to)810-814
Number of pages5
JournalNature Chemistry
Volume6
Issue number9
Early online date27 Jul 2014
DOIs
Publication statusPublished - 1 Sep 2014

Fingerprint Dive into the research topics of 'Synthesis of hydroxyphthioceranic acid using a traceless lithiation-borylation-protodeboronation strategy'. Together they form a unique fingerprint.

Cite this