6739-80-6Relevant articles and documents
Quaternary Charge-Transfer Complex Enables Photoenzymatic Intermolecular Hydroalkylation of Olefins
Page, Claire G.,Cooper, Simon J.,Dehovitz, Jacob S.,Oblinsky, Daniel G.,Biegasiewicz, Kyle F.,Antropow, Alyssa H.,Armbrust, Kurt W.,Ellis, J. Michael,Hamann, Lawrence G.,Horn, Evan J.,Oberg, Kevin M.,Scholes, Gregory D.,Hyster, Todd K.
supporting information, p. 97 - 102 (2021/01/12)
Intermolecular C-C bond-forming reactions are underdeveloped transformations in the field of biocatalysis. Here we report a photoenzymatic intermolecular hydroalkylation of olefins catalyzed by flavin-dependent 'ene'-reductases. Radical initiation occurs via photoexcitation of a rare high-order enzyme-templated charge-transfer complex that forms between an alkene, α-chloroamide, and flavin hydroquinone. This unique mechanism ensures that radical formation only occurs when both substrates are present within the protein active site. This active site can control the radical terminating hydrogen atom transfer, enabling the synthesis of enantioenriched γ-stereogenic amides. This work highlights the potential for photoenzymatic catalysis to enable new biocatalytic transformations via previously unknown electron transfer mechanisms.
Synthesis of an azabicyclic framework towards (±)-actinophyllic acid
Mortimer, Danny,Whiting, Matthew,Harrity, Joseph P.A.,Jones, Simon,Coldham, Iain
, p. 1255 - 1257 (2014/02/14)
Lewis acid mediated intramolecular Mannich reaction between an azocinone and a 3-formylindole was investigated as part of a study towards the synthesis of actinophyllic acid. The intramolecular Mannich reaction resulted in a single diastereomer of the 1-azabicyclo[4.2.1]nonan-5-one core framework, although single crystal X-ray structure analysis revealed that this had the undesired stereochemistry in comparison with the natural product.
Synthesis of Δ1- and/or Δ8-Dehydroindolizidines and Related Compounds
Miyano, Seiji,Fujii, Shinichiro,Yamashita, Osamu,Toraishi, Naoko,Sumoto, Kunihiro
, p. 1465 - 1468 (2007/10/02)
A facile synthesis of Δ1- and/or Δ8-dehydroindolizidine and related compounds, consisting of dry distillation of γ-(N-2-piperidinonyl)butyric acid over soda-lime, is described.Reductions of these dehydroindolizidines and stereochemistry of 1-methylindolizidine are also described.