<p>Tuberculosis is an infectious disease caused by <i>Mycobacterium tuberculosis</i> and is one of the most dangerous and socially significant diseases. The growth and expanding spectrum of drug resistance of <i>M. tuberculosis</i> makes it necessary to design new anti-tuberculosis pharmaceuticals with alternative mechanism of action. In this study, original synthetic routes to the novel conjugates of <i>closo</i>- and <i>nido</i>-carboranes and monoterpenes (geraniol, nerol, and citronellol) attached via linkers were proposed. Monoterpene derivatives were obtained starting from <i>closo</i>- and <i>nido</i>-carborane-containing building blocks with carboxyl or chloroethyl groups. The structures of all synthesized molecules were confirmed by ¹H, ¹³C and ¹¹B NMR, and ESI–MS. Antimycobacterial activity of the synthesized compounds against the standard drug-sensitive laboratory strain <i>M. tuberculosis</i> H37Rv using the REMA method was assessed. It has been found that <i>nido</i>-carborane conjugates with monoterpene residues attached via an ethylenediamine linker exhibit weak inhibitory activity against the <i>M. tuberculosis</i> H37Rv strain in in vitro experiments; amides of (<i>closo</i>-carboran-1-yl)acetic acid containing monoterpene residues did not exhibit antimycobacterial activity. The developed method can be applied to obtain various bioactive <i>nido</i>-carborane derivatives.</p> Graphical Abstract <p></p>