Jump to main content
Jump to site search

Issue 43, 2016
Previous Article Next Article

The effect of backbone flexibility on site-selective modification of macrocycles

Author affiliations

Abstract

As the emerging modality in drug discovery, macrocycles represent topical targets of chemical synthesis. However, the influence of conformational effects on their reactivity has not received enough attention. We demonstrate that the regiochemistry of nucleophilic attack on aziridine-containing macrocyclic systems varies according to macrocycle ring size and that the influence of remote torsional interactions in the macrocycle ultimately determines the regioselectivity of the reactions. These findings should facilitate the development of divergent strategies of macrocycle synthesis using post-cyclization modification.

Graphical abstract: The effect of backbone flexibility on site-selective modification of macrocycles

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 15 Aug 2016, accepted on 06 Oct 2016 and first published on 06 Oct 2016


Article type: Paper
DOI: 10.1039/C6OB01778A
Citation: Org. Biomol. Chem., 2016,14, 10230-10237
  •   Request permissions

    The effect of backbone flexibility on site-selective modification of macrocycles

    C. C. G. Scully, C. J. White and A. K. Yudin, Org. Biomol. Chem., 2016, 14, 10230
    DOI: 10.1039/C6OB01778A

Search articles by author