A concise, enantioselective total synthesis of the Lycopodium alkaloid (-)-lyconadin C was achieved in 12 steps and high overall yield. Key features include construction of a luciduline congener through Mannich-type cyclization and a one-pot, tandem Curtius rearrangement/6π-electrocyclization to fashion the 2-pyridone system of lyconadin C.
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http://dx.doi.org/10.1021/ol401954f | DOI Listing |
Macromol Rapid Commun
February 2023
Department of Chemistry, Sungkyunkwan University, (16419) 2066, Seobu-ro, Jangan-gu, Suwon-si, Gyeonggi-do, Republic of Korea.
The design and synthesis of phthalimide derivatives are important goals for applications in fields such as pharmaceutical science and optoelectronics. In the present study, a facile and convenient synthetic pathway (no heat or acid/catalyst needed) is devised to produce phthalimides from a biomass-derived furan by directly introducing an N-carbamate group at the C-2 position of the furan ring via thermal Curtius rearrangement. The electron-donating N-carbamate group increases the energy level of the highest occupied molecular orbital of the furan diene, resulting in a significant increase of the rate of the Diels-Alder reaction with maleimide compared to the conventional furfuryl furan.
View Article and Find Full Text PDFEur J Med Chem
December 2017
Department of Organic Chemistry, Nizhny Novgorod State University, Gagarina Av. 23, 603950 Nizhny Novgorod, Russian Federation. Electronic address:
Two novel indole-containing allocolchicinoids were prepared from naturally occurring colchicine exploiting the Curtius rearrangement and tandem Sonogashira coupling/Pd-catalyzed cyclization as the key transformations. Their cytotoxic properties, apoptosis-inducing activity, tubulin assembly inhibition and short-time cytotoxic effects were investigated. Compound 7 demonstrated the most pronounced anti-cancer activity: IC < 1 nM, cell cycle arrest in the G2/M phase, 25% apoptosis induction, as well as lower destructive short-time effects on HT-29 cell line in comparison with colchicine.
View Article and Find Full Text PDFJ Org Chem
January 2017
Department of Pharmaceutical Sciences, Bouvé College of Health Sciences, Northeastern University, 140 The Fenway, 360 Huntington Avenue, Boston, Massachusetts 02115, United States.
We report a facile, microwave-accelerated, one-pot tandem synthesis of unsymmetrical ureas via a Curtius rearrangement. In this method, one-pot microwave irradiation of commercially available (hetero)aromatic acids and amines in the presence of diphenylphosphoryl azide enabled extremely rapid (1-5 min) construction of an array of unsymmetrical ureas in good to excellent yields. We demonstrate the utility of our method in the efficient, gram-scale synthesis of key biologically active compounds targeting the cannabinoid 1 and α7 nicotinic acetylcholine receptors.
View Article and Find Full Text PDFOrg Lett
August 2013
Department of Chemistry, The University of Vermont, 82 University Place, Burlington, Vermont 05405, USA.
A concise, enantioselective total synthesis of the Lycopodium alkaloid (-)-lyconadin C was achieved in 12 steps and high overall yield. Key features include construction of a luciduline congener through Mannich-type cyclization and a one-pot, tandem Curtius rearrangement/6π-electrocyclization to fashion the 2-pyridone system of lyconadin C.
View Article and Find Full Text PDFAnal Chem
June 2009
Helmholtz Zentrum München, Institute of Ecological Chemistry, 85764 Neuherberg, Germany.
An in-house-built ion trap mass spectrometer combined with a soft ionization source has been set up and tested. As ionization source, an electron beam pumped vacuum UV (VUV) excimer lamp (EBEL) was used for single-photon ionization. It was shown that soft ionization allows the reduction of fragmentation of the target analytes and the suppression of most matrix components.
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