Toward Pyridine-Heterocycle Patterns through Prins and Aza-Prins Cyclisations: Application to a Short Synthesis of (±)-Anabasine
作者： Olivier Colin , Christine Greck , Damien Prim , Christine Thomassigny
关键词: Stereochemistry 、 Pyridine 、 Chemistry 、 Organic chemistry 、 Amine gas treating 、 Prins reaction 、 Sequence (biology) 、 Anabasine 、 Alkaloid
摘要: The formation of pyridine-containing bisheterocycles through a Prins-type cyclisation is described. Pyridine–tetrahydropyran and pyridine–piperidine conjugates could be efficiently obtained using various carbaldehydes including dicarbaldehydes, either homoallylic alcohols or amine. Selective partial complete hydrogenation led to new bisheterocycle combinations. A two-step sequence involving an aza-Prins cylisation allowed us prepare the alkaloid anabasine.
sci-hub.se 参考文章(29)
Romain Sallio, Stéphane Lebrun, Nicolas Gigant, Isabelle Gillaizeau, Eric Deniau, Asymmetric Synthesis of 2-Heteroaryl Cyclic Amines: Total Synthesis of (–)-Anabasine European Journal of Organic Chemistry. ,vol. 2014, pp. 4381- 4388 ,(2014) , 10.1002/EJOC.201402202
Alexandre Larivée, James J. Mousseau, André B. Charette, Palladium-catalyzed direct C-h arylation of N-iminopyridinium ylides: application to the synthesis of (+/-)-anabasine. Journal of the American Chemical Society. ,vol. 130, pp. 52- 54 ,(2008) , 10.1021/JA710073N
Géraldine Le Bouc, Christine Thomassigny, Christine Greck, Diastereoselective syntheses of 1-deoxyhomonojirimycin and two new 1,5,6-trideoxy-1,5-iminoheptitols with d-allo- and l-talo-configuration Tetrahedron-asymmetry. ,vol. 17, pp. 2006- 2014 ,(2006) , 10.1016/J.TETASY.2006.07.022
J.S. Yadav, B.V. Subba Reddy, K. Ramesh, G.G.K.S. Narayana Kumar, René Grée, A novel aza-Prins-Friedel-Crafts reaction for the synthesis of 4-arylpiperidines Tetrahedron Letters. ,vol. 51, pp. 818- 821 ,(2010) , 10.1016/J.TETLET.2009.12.007
G.William Daub, Dirt A. Heerding, Larry E. Overman, Synthesis of substituted tetrahydropyridines by cyclizations of silicon-containing iminium ions Tetrahedron. ,vol. 44, pp. 3919- 3930 ,(1988) , 10.1016/S0040-4020(01)86645-X
Artur Noole, Kristin Lippur, Andrus Metsala, Margus Lopp, Tõnis Kanger, Enantioselective Henry Reaction Catalyzed by CuII Salt and Bipiperidine Journal of Organic Chemistry. ,vol. 75, pp. 1313- 1316 ,(2010) , 10.1021/JO902664V
B.V. Subba Reddy, K. Ramesh, A.V. Ganesh, G.G.K.S. Narayana Kumar, J.S. Yadav, René Grée, Triflic acid-promoted aza-Prins-Ritter reaction sequence: a novel synthesis of 4-amidopiperidine derivatives Tetrahedron Letters. ,vol. 52, pp. 495- 498 ,(2011) , 10.1016/J.TETLET.2010.11.060
Timothy K. Beng, Robert E. Gawley, Application of catalytic dynamic resolution of N-Boc-2-lithiopiperidine to the asymmetric synthesis of 2-aryl and 2-vinyl piperidines. Organic Letters. ,vol. 13, pp. 394- 397 ,(2011) , 10.1021/OL102682R
Damien Clarisse, Béatrice Pelotier, Fabienne Fache, Solvent-Free, Metal-Free, Aza-Prins Cyclization: Unprecedented Access to δ-Sultams Chemistry - A European Journal. ,vol. 19, pp. 857- 860 ,(2013) , 10.1002/CHEM.201203415
Tiina Saloranta, Reko Leino, From building block to natural products: a short synthesis and complete NMR spectroscopic characterization of (±)-anatabine and (±)-anabasine Tetrahedron Letters. ,vol. 52, pp. 4619- 4621 ,(2011) , 10.1016/J.TETLET.2011.06.093