Abstract
This thesis work focuses on the synthesis of macrotermycin A, a natural macrolactam with promising antibiotic and antifungal properties. The structural complexity of this compound led us to a convergent synthetic approach based on the creation of 2 main fragments of similar sizes.Initially, we focused our efforts on the synthesis of the first fragment, drawing our inspiration from the work carried out by Tsuboi et al., which described the conversion of a propargyl alcohol into a E,Z diene ester by a sequence composed of a Johnson-Claisen rearrangement and subsequent isomerization on alumina.For the synthesis of the second fragment, we relied on an asymmetric copper-catalyzed vinylogous Mukaiyama reaction in order to form in a single step, two contiguous stereogenic centers, including one quaternary, and a Z double bond.In parallel, we got interested in the synthesis of different compounds derived from biological intermediates allowing to simplify the study of the biosynthesis of macrotermycin A.