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
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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
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
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Graphical Abstract
Figure 1:
Sansalvamide A (1) and its depsipeptoid analogues (2).