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

• reaction under pseudo-high dilution conditions (to avoid oligomerization) to furnish cyclopeptoids 85 and 90, respectively (Scheme 16 and Scheme 17). Ester hydrolysis and N-deprotection reactions were carried out in between. In this approach, by varying the amine component, the side chains of the peptoid

Selectivity in multiple multicomponent reactions: types and synthetic applications

• Ouldouz Ghashghaei,
• Francesca Seghetti and
• Rodolfo Lavilla

Beilstein J. Org. Chem. 2019, 15, 521–534, doi:10.3762/bjoc.15.46

• same strategy was exploited by Wessjohann for the synthesis of RGD (Arg-Gly-Asp)cyclopeptoids [51]. In this case, they developed a stepwise protocol in which two Ugi 4CRs, flanking a deprotection, provided linear peptidic adducts. Afterwards, these intermediates were again deprotected and a final Ugi

• sequence. High order MMCRs. A) Ugi/Ugi–Smiles 7C combination; B) imidazoline-N-cyanomethylamide-Ugi union leading to an 8CR. Consecutive Ugi 4CR-deprotection–Ugi 4CR strategy towards A) PNA oligomers and B) peptidic tetrazoles and hydantionimides. Sequential Ugi 4CR-deprotection access to cyclopeptoids

Synthesis of the first examples of iminosugar clusters based on cyclopeptoid cores

• Mathieu L. Lepage,
• Alessandra Meli,
• Anne Bodlenner,
• Céline Tarnus,
• Francesco De Riccardis,
• Irene Izzo and
• Philippe Compain

Beilstein J. Org. Chem. 2014, 10, 1406–1412, doi:10.3762/bjoc.10.144

• . Keywords: cyclopeptoids; glycosidases; iminosugars; inhibitors; multivalency; mutivalent glycosystems; Introduction Within a few years, the field of multivalent glycosidase inhibitors has witnessed tremendous advancement. Since the report in 2009 of the first quantifiable multivalent effect in glycosidase

• reported [22][23][24][25][26][27][28][29][30][31] and few of them are related to cyclopeptoids [32][33]. One of the most intriguing features of peptoids is their capacity to generate cyclic structures, which can expand the utility of this platform to multivalent chemical achitectures [34]. Conformation

• context cyclopeptoids 2–4 appear as ideal building blocks because of their simplicity of synthesis and easy functionalization by click reaction (Figure 1). In the present paper, we report the synthesis of the first examples of cyclopeptoid-based iminosugar clusters. The influence of valency, size, linker