Current commercial routes to delamanid involve the generation of key chiral epoxide intermediates 3a and 6 (Scheme 1). These building blocks introduce not only the required chirality but also a functional handle for further derivatization. The epoxide can be derived either directly from an allylic alcohol 5 via a Sharpless epoxidation, or from a more advanced intermediate 7a via a three-step process commencing with a Sharpless dihydroxylation. Both routes employ robust asymmetric methodologies to introduce the epoxide with high levels of enantioselectivity. However, these processes rely on either the use of precious metal titanium or toxic osmium catalysts respectively. Moreover, the Sharpless epoxidation must be performed on an underivatized allylic alcohol. This introduces extra subsequent steps downstream as the epoxide must be reformed after initial opening to incorporate both the imidazole and phenolic fragments present in delamanid. Similarly, additional steps are required to convert the chiral diol dihydroxylation product into the electrophilic chiral epoxide, as a Sharpless asymmetric epoxidation cannot be performed directly on the more advanced fragment. Development of a method whereby the advanced unactivated terminal alkene could undergo direct highly selective epoxidation would allow streamlining of the synthetic route to delamanid. Increasingly, biocatalysis is viewed as an attractive alternative to transition metal-catalyzed transformations for the manufacture Scheme 1: Retrosynthetic analysis of delamanid and current approaches for the synthesis of the chiral epoxide intermediates.