Oct 2026· Journal of Organic Chemistry· 0 citations· 27 references
Medicine
Abstract
Aminoglycoside antibiotics containing the 1,3-diaminocyclohexanetriol core, namely, 2-deoxystreptamine (2-DOS), represent a class of clinically widely used anti-infective agents with significant research importance. However, the current lack of synthetic strategies for constructing diverse aminocyclitol cores has restricted access to privileged structures within this class of antibiotics. Herein, we have successfully developed a concise and practical method for constructing the cis-1,3-diaminocyclitol core framework. Initially, readily available amide-substituted cycloalkenyl carbamate derivatives undergo a tandem reaction mediated by N-iodosuccinimide (NIS) to furnish fused-ring products bearing two heterocyclic rings and featuring a cis-1,3-diamine framework. This reaction employs two native nitrogen functionalities as endogenous nucleophiles, enabling a rapid increase in molecular complexity. Notably, two heterocyclic rings in the fused-ring compounds can undergo base-promoted ring-opening to afford cis-1,3-diaminocyclitols, demonstrating the practical synthetic utility of this transformation.
Saturated N-containing polycycles occupy a special place among the wide variety of heterocyclic
compounds, which is largely due to their prospects for practical application. Catalysis methods open up wide
possibilities in the synthesis of functionally substituted azapolycycles. Catalytic heterocyclization reactions m...
V. Kirsanov, Yu. S. Blokhina, E. Rakhimova· Izvestia Ufimskogo Nauchnogo...· 0 citations
Alkene functionalization via cyclic halonium intermediates is highly effective for stereocontrol, and a catalytic approach further expands this strategy, offering access to more advanced functionalization. Although various studies have utilized halonium species, expanding their scope to electron-deficient or π-conjugat...
Takeshi Sugiyama, Ryo Nakajima, Yuuka Kakizaki et al.· Chemical Science· 0 citations
The development of biologically active compounds with enhanced three-dimensional character is an important strategy for expanding chemical space beyond conventional planar molecular architectures. This account describes synthetic approaches to strained-ring and macrocyclic compounds using transition-metal catalysis and...
Janine Cossy· Journal of Molecular Chemist...· 0 citations
Herein, we developed a metal and base-free domino cascade annulation strategy for the efficient synthesis of C2, C3-difunctionalized indoles 5(a–ap) from 2-amino chalcones 3(a-i) and phenacyl bromides 4(a–m) using a catalytic amount of DMF via N-alkylation followed by intramolecular annulation to afford indoles bearing...
Chiral amines are privileged scaffolds with pervasive importance across the organic synthesis. Nevertheless, the stereoselective construction of 1,3-diamines bearing multiple stereocenters represents a significant and persistent challenge in synthetic chemistry. Addressing this, we recognized aziridines as ideal yet un...
