Synthesis of (macro)heterocycles by consecutive/repetitive isocyanide-based multicomponent reactions

• Angélica de Fátima S. Barreto and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2019, 15, 906–930, doi:10.3762/bjoc.15.88

• methodology was used in the synthesis of six cyclic depsipeptoids inspired by the structure of the natural depsipeptide sansalvamide A, which involved five steps (Scheme 19). In the first step, formation of the peptoid was achieved via the first Ugi reaction. Then, subsequent hydrolysis of the ester was

• cyclic depsipeptoids 100a–f in yields ranging from 33–49% depending on the substrate. More recently, our research group described a fast and efficient strategy for the synthesis of macrocycles using four consecutive Ugi reactions (Scheme 20) [35]. This was the first example in the literature in which

Consecutive isocyanide-based multicomponent reactions: synthesis of cyclic pentadepsipeptoids

• Angélica de Fátima S. Barreto,
• Otilie E. Vercillo,
• Ludger A. Wessjohann and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2014, 10, 1017–1022, doi:10.3762/bjoc.10.101

• Nossa Senhora de Fátima, Planaltina, 73300-000, Brasília, DF, Brazil Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle (Saale), Germany 10.3762/bjoc.10.101 Abstract The synthesis of six cyclic depsipeptoids inspired by the natural depsipeptide

• sansalvamide A is described. An efficient and fast synthetic strategy was developed using a combination of consecutive isocyanide-based multicomponent reactions (Ugi and Passerini reactions). This methodology can be used to access a variety of cyclic oligodepsipeptoids. Keywords: depsipeptoids; multicomponent

• in combinatorial synthesis [40][41][42][43] and can be used strategically for the synthesis of depsipeptoids. By analogy to peptides and peptoids, a depsipeptoid would be a peptoid bearing an ester group instead of an amide group. Differences between peptide, peptoid, depsipeptide and depsipeptoid