2. Academic Validation
  3. Matteson Homologation-Based Total Synthesis of Meliponamycin A

Matteson Homologation-Based Total Synthesis of Meliponamycin A

  • Org Lett. 2024 Jan 12;26(1):148-152. doi: 10.1021/acs.orglett.3c03766.
Oliver Andler 1,  Uli Kazmaier 1
Affiliations

Affiliation

  • 1 Organic Chemistry I, Saarland University, Campus Building C4.2, D-66123 Saarbrücken, Germany.
PMID: 38147843 DOI: 10.1021/acs.orglett.3c03766
Abstract

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.

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