Iboxamycin

The prolonged and incorrect use of antibiotics over decades has facilitated the development of antibiotic resistance which is a major threat to the future of public health. Indeed, without the development of new methods to treat bacterial infection we risk passing into a post-antibiotic age. The identification of next-generation antibacterial small molecules is therefore of paramount importance.

This week our synthetic organic chemistry problem session group have been studying the gram scale synthesis of iboxamycin, a novel antibiotic with activity against both Gram-positive and -negative bacteria, over 15 synthetic steps – no mean feat: https://pubs.acs.org/doi/10.1021/jacs.1c03529

We learned about the use of pseudoephenamine as a chiral auxiliary for asymmetric enolate alkylations. The protocol for the sp3 – sp2 zinc-catalysed Negishi coupling was also interesting – we have carried out this type of reaction on tens of gram scale in our research laboratory at Concept Life Sciences.