Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor

• Yuki Naito,
• Naoki Shida and
• Mahito Atobe

Beilstein J. Org. Chem. 2022, 18, 350–359, doi:10.3762/bjoc.18.39

• , natural products, and biologically active compounds such as pergolide, scopolamine, morphine, nicotine, hygrine, and procyclidine (Figure 1) [2][3][4]. Therefore, a considerable number of synthetic approaches to pyrrolidines and piperidines have been investigated [5][6][7][8][9][10][11][12][13

Chemical tuning of photoswitchable azobenzenes: a photopharmacological case study using nicotinic transmission

• Lorenzo Sansalone,
• Jun Zhao,
• Matthew T. Richers and
• Graham C. R. Ellis-Davies

Beilstein J. Org. Chem. 2019, 15, 2812–2821, doi:10.3762/bjoc.15.274

• fundamentally different categories which were defined, historically, using pharmacology. The neurotransmitter-gated ion channels are activated by the drug nicotine, and these are called nicotinic (n)AChR. The G-protein-coupled receptors are activated by the drug muscarine, and these are called muscarinic (m

• )AChR. The structural difference between the native acetylcholine and nicotine are striking, and their diversity reflects the complexity of structure–activity relationships of ligands for nicotinic acetylcholine receptors. For example, the drug homocholine phenyl ether (HoChPE) is an agonist of the

Semi-synthesis and insecticidal activity of spinetoram J and its D-forosamine replacement analogues

• Kai Zhang,
• Jiarong Li,
• Honglin Liu,
• Haiyou Wang and
• Lamusi A

Beilstein J. Org. Chem. 2018, 14, 2321–2330, doi:10.3762/bjoc.14.207

• spinosyn molecule interacts with both gamma-aminobutyric acid (GABA) receptor and nicotine acetylcholine (NACh) receptors [9]. Spinosad and spinetoram can be degraded via a combination of photolysis and microbial action, ultimately producing CO2, H2O, and nitrogen oxides [10]. That suggests that along with

The enzymes of microbial nicotine metabolism

• Paul F. Fitzpatrick

Beilstein J. Org. Chem. 2018, 14, 2295–2307, doi:10.3762/bjoc.14.204

• deal of interest in identifying bacteria capable of degrading it. A number of microbial pathways have been identified for nicotine degradation. The first and best-understood is the pyridine pathway, best characterized for Arthrobacter nicotinovorans, in which the first reaction is hydroxylation of the

• steps in the pyrrolidine pathway. This review summarizes the present status of our understanding of these pathways, focusing on what is known about the individual enzymes involved. Keywords: biodegradation; enzyme mechanism; flavoprotein; metabolic pathway; nicotine; Introduction The toxic alkaloid (S

• )-nicotine (L-nicotine) is found at high levels in tobacco leaves and the waste from tobacco processing. The resulting interest in developing environmentally friendly methods of degrading nicotine has driven studies of microbial pathways for metabolizing the compound, with the possible additional benefit of

A strategic approach to [6,6]-bicyclic lactones: application towards the CD fragment of DHβE

• Tue Heesgaard Jepsen,
• Emil Glibstrup,
• François Crestey,
• Anders A. Jensen and
• Jesper Langgaard Kristensen

Beilstein J. Org. Chem. 2017, 13, 988–994, doi:10.3762/bjoc.13.98

• extensively investigated as potential drug targets for a diverse array of central nervous system (CNS) related medical conditions such as Alzheimer’s and Parkinson’s disease, depression, ADHD, pain relief, nicotine addiction and drug abuse [1]. Dihydro-β-erythroidine (DHβE) is a member of the family of

An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2013, 9, 2265–2319, doi:10.3762/bjoc.9.265

• including nicotine, pyridine, is thus important for a wide range of biological activities [8]. Consequently, the pyridine ring is utilised in many pharmaceutical actives and possibly even more commonly found in agrochemical products. This can be rationalised by the fact that simple pyridines readily undergo

Palladium-catalyzed dual C–H or N–H functionalization of unfunctionalized indole derivatives with alkenes and arenes

• Gianluigi Broggini,
• Egle M. Beccalli,
• Andrea Fasana and
• Silvia Gazzola

Beilstein J. Org. Chem. 2012, 8, 1730–1746, doi:10.3762/bjoc.8.198

• pyridine or nicotine platforms (PyOx and NicOx, respectively) [68][69]. A moderate level of enantiocontrol (up to 51 % ee) was seen in 5-exo-trig cyclization of the 3-alkenylindole 19 (n = 1) in the presence of ligands 20 and 21, to yield 22, whilst the outcome of the 6-exo-trig cyclization of indole 19 (n