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 sansalvamideA, 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
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Graphical Abstract
Scheme 1:
Comparison between a normal sequential reaction and an MCR.
Beilstein J. Org. Chem.2014,10, 1017–1022, doi:10.3762/bjoc.10.101
sansalvamideA 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; sansalvamideA; 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 sansalvamideA (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
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Graphical Abstract
Figure 1:
Sansalvamide A (1) and its depsipeptoid analogues (2).