92647-37-5Relevant articles and documents
Taming Radical Pairs in the Crystalline Solid State: Discovery and Total Synthesis of Psychotriadine
Dotson, Jordan J.,Liepuoniute, Ieva,Bachman, J. Logan,Hipwell, Vince M.,Khan, Saeed I.,Houk,Garg, Neil K.,Garcia-Garibay, Miguel A.
, p. 4043 - 4054 (2021/04/06)
Solid-state photodecarbonylation is an attractive but underutilized methodology to forge hindered C-C bonds in complex molecules. This study discloses the use of this reaction to assemble the vicinal quaternary stereocenter motif present in bis(cyclotryptamine) alkaloids. Our strategy was enabled by experimental and computational investigations of the role of substrate conformation on the success or failure of the solid-state photodecarbonylation reaction. This informed a crystal engineering strategy to optimize the key step of the total synthesis. Ultimately, this endeavor culminated in the successful synthesis of the bis(cyclotryptamine) alkaloid "psychotriadine,"which features the elusive piperidinoindoline framework. Psychotriadine, a previously unknown compound, was identified in the extracts of the flower Psychotria colorata, suggesting it is a naturally occurring metabolite.
Potential GABAB Receptor Antagonists. X* the Synthesis of Further Analogues of Baclofen, Phaclbfen and Saclofen
Prager, Rolf H.,Schafer, Karl
, p. 813 - 823 (2007/10/03)
In an attempt to obtain new compounds with binding activity at the GABAB receptor site, we report the synthesis of 3-amino-2-arylpropanoic acids, and the sulfonic, phosphonic and hydroxamic acid analogues. In addition, we report the synthesis of the isomer of phaclofen, 3-amino-1-(4-chlorophenyl)-propylphosphonic acid, and the higher homologue of baclofen, 5-amino-2-(4-chlorophenyl)pentanoic acid.
