261620-76-2Relevant academic research and scientific papers
PdII-Mediated Oxidative Amination for Access to a 9-Azabicyclo[4.2.1]nonane Compound Library and Anatoxin-a
Dawood, Rafid S.,Chidipudi, Suresh R.,O'Connor, Daniel C.,Lewis, William,Hamza, Daniel,Pearce, Christopher A.,Jones, Geraint,Wilkie, Ross P.,Georgiou, Irene,Storr, Thomas E.,Moore, Jonathan C.,Stockman, Robert A.
supporting information, p. 5558 - 5561 (2018/10/26)
Intramolecular oxidative amination of readily accessible aminocyclooct-4-enes provides rapid and regioselective access to the 9-azabicyclo[4.2.1]nonane framework characteristic of the natural product anatoxin-a (1). This has enabled the synthesis of sp3-rich chemical scaffolds suitable for diversification. A library of 881 lead-like compounds is reported alongside a formal synthesis of anatoxin-a (1).
A new strategy to produce β-peptides: Use of alicyclic β-lactams
Fül?p, Ferenc,Forró, Enik?,Tóth, Gábor K.
, p. 4239 - 4241 (2007/10/03)
(Chemical Equation Presented) On p-methylbenzhydrylamine (MBHA) resin, by means of t-Boc chemistry, several tetrapeptides (H-Ala-ACXC-Ala-Gly-NH 2) containing cyclic β-amino acid units were prepared. These units were introduced into the growing peptide chain by using Boc-protected β-lactams with KCN as catalyst in DMF. The method was applicable for both racemic and enantiomeric β-lactams.
Synthesis of (±)-anatoxin-α and analogues
Parsons, Philip J.,Camp, Nicholas P.,Edwards, Neil,Ravi Sumoreeah
, p. 309 - 315 (2007/10/03)
A new and highly efficient synthesis of the potent nicotinic acetylcholine receptor agonist, anatoxin-α and its analogues is described, which uses a β-lactam ring opening-transannular cyclisation sequence to set up the bridged bicyclic framework of the natural product. The synthesis involves a cycloaddition of chlorosulfonyl isocyanate with cyclooctadiene followed by Boc protection of the resulting β-lactam. Reaction of the β- lactam with a variety of nucleophiles, followed by selenium-mediated cyclisation and oxidation gave the skeleton of anatoxin-α bearing various sidechains. The approach offers a flexible entry to useful quantities of anatoxin-α and its analogues.
