10.1002/ejoc.200400213
The research focuses on the synthesis of a small library of highly electron-rich 2-aryl and 2-heteroaryl phenethylamines (PEAs) using the Suzuki-Miyaura cross-coupling reaction, which is enhanced by microwave irradiation for improved reaction yield and speed. The study commenced with the synthesis of benzyl [2-(2-bromo-4,5-dimethoxyphenyl)ethyl]carbamate from 2-(3,4-dimethoxyphenyl)ethylamine, followed by its coupling with various boronic acids to generate the PEAs. The reactions were optimized using sodium hydrogencarbonate as the base and tetrakis(triphenylphosphane)palladium(0) as the catalyst, with the mixture of N,N-dimethylformamide and water as the solvent. The synthesized compounds were characterized by 1H and 13C NMR spectroscopy, and low-resolution mass spectrometry (LR-MS) to confirm their structures and purities. The research also successfully extended this methodology to synthesize an apogalanthamine analogue, a complex natural product with significant biological activities, showcasing the versatility and efficacy of the developed synthetic strategy.
10.1002/ejoc.201800611
The study presents a concise synthesis of lamellarin G trimethyl ether, a pyrrole alkaloid with significant pharmacological properties, through a von Miller-Pl?chl type cyclocondensation. The key chemicals used include α-amino nitrile, α,β-unsaturated ketone, and various building blocks such as arylboronic acid, enone, and homoveratrylamine. These chemicals serve as precursors and reactants in the synthesis process, which is divided into two routes, with the cyclocondensation reaction as the key step. The study aims to develop a modular synthetic strategy that allows for the independent variation of the substitution pattern in the lamellarin molecule, providing a high-yielding and efficient method for synthesizing lamellarin G trimethyl ether, which is often used as a benchmark compound in evaluating synthetic approaches to the lamellarins.
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