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

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

• 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

• reactions; Passerini reaction; sansalvamide A; Ugi reaction; Introduction Peptoids are an interesting class of non-natural compounds that have recently received much attention due to their wide range of biological activities, which makes them attractive candidates for drug discovery [1][2][3][4][5][6][7

• cyclic depsipeptide is sansalvamide A (San A, Figure 1) [20][21][22][23][24][25][26][27][28][29], which was isolated from a marine fungus (Fusarium spp.) [20] and exhibits antitumor activity against multiple cancer cell lines. It is cytotoxic against colon (HCT-116) [20][23][25][26], pancreatic (S2-013