218900-31-3Relevant academic research and scientific papers
Total synthesis of biseokeaniamides A-C and late-stage electrochemically-enabled peptide analogue synthesis
Lin, Yutong,Malins, Lara R.
, p. 10752 - 10758 (2020/10/26)
The first total synthesis of cytotoxic cyanobacterial peptide natural products biseokeaniamides A-C is reported employing a robust solid-phase approach to peptide backbone construction followed by coupling of a key thiazole building block. To rapidly access natural product analogues, we have optimized an operationally simple electrochemical oxidative decarboxylation-nucleophilic addition pathway which exploits the reactivity of native C-terminal peptide carboxylates and abrogates the need for building block syntheses. Electrochemically-generated N,O-acetal intermediates are engaged with electron-rich aromatics and organometallic reagents to forge modified amino acids and peptides. The value of this late-stage modification method is highlighted by the expedient and divergent production of bioactive peptide analogues, including compounds which exhibit enhanced cytotoxicity relative to the biseokeaniamide natural products. This journal is
Selective Monomethylation of Amines with Methanol as the C1 Source
Choi, Geunho,Hong, Soon Hyeok
, p. 6166 - 6170 (2018/04/30)
The N-monomethyl functionality is a common motif in a variety of synthetic and natural compounds. However, facile access to such compounds remains a fundamental challenge in organic synthesis owing to selectivity issues caused by overmethylation. To address this issue, we have developed a method for the selective, catalytic monomethylation of various structurally and functionally diverse amines, including typically problematic primary aliphatic amines, using methanol as the methylating agent, which is a sustainable chemical feedstock. Kinetic control of the aliphatic amine monomethylation was achieved by using a readily available ruthenium catalyst at an adequate temperature under hydrogen pressure. Various substrates including bio-related molecules and pharmaceuticals were selectively monomethylated, demonstrating the general utility of the developed method.
Ligand-controlled α- And β-arylation of acyclic N-boc amines
Millet, Anthony,Dailler, David,Larini, Paolo,Baudoin, Olivier
, p. 2678 - 2682 (2014/03/21)
The palladium-catalyzed ligand-controlled arylation of α-zincated acyclic amines, obtained by directed α-lithiation and transmetalation, is described. Whereas PtBu3 gave rise to α-arylated Boc-protected amines, more flexible N-phenylazole-based phosphine ligands induced major β-arylation through migrative cross-coupling. All manner of control: The arylation of α-zincated acyclic Boc-protected amines was selectively performed at the α- or β-position in a ligand-controlled manner. α-Arylation occurs by direct reductive elimination of the α-palladated intermediate whereas β-arylation involves palladium migration along the alkyl chain. Boc=tert-butoxycarbonyl.
Nucleophilic substitution reaction at the nitrogen of arylsulfonamides with phosphide anion
Yoshida, Suguru,Igawa, Kazunobu,Tomooka, Katsuhiko
supporting information, p. 19358 - 19361 (2013/02/22)
A novel nucleophilic substitution reaction at the nitrogen of arylsulfonamides by means of phosphide anions has been described. This reaction allows for the efficient transformation of arylsulfonamides into synthetically valuable phosphamides, amines, and a variety of protected amines.
