Matteson Homologation-Based Total Synthesis of Meliponamycin A.
Oliver AndlerUli KazmaierPublished in: Organic letters (2023)
The first total synthesis of meliponamycin A, an antimicrobial cyclodepsipeptide isolated from Streptomyces , is reported. Two key building blocks, the substituted tetrahydropyranyl side chain and an azido analogue of protected β-hydroxyleucine, were constructed via iterative Matteson homologations. A fragment coupling of a tetrapeptide, a depsidipeptide building block, macrocyclization, Staudinger reduction, and N -acylation are further steps in the synthesis.