Stereoselective Synthesis of Trifluoromethyl Analogues of Polyhydroxypyrrolidines

作者: Rama K. Khangarot , Krishna P. Kaliappan

DOI: 10.1002/EJOC.201201599

关键词: ChemistryFluorineSolubilityMoleculeNucleophilic additionBond cleavageOrganic chemistrySilaneTrifluoromethylStereoselectivity

摘要: Incorporation of fluorine atoms into organic molecules significantly enhances many their properties, such as solubility, metabolic stability, and bioavailability. Among organofluorine molecules, trifluoromethylated compounds play a unique important role in agricultural medicinal chemistry. An efficient strategy for the synthesis variety polyhydroxypyrrolidines is described. This involves diastereoselective nucleophilic addition reaciton trimethyl(trifluoromethyl)silane to sugar-derived cyclic nitrones followed by reductive N–O bond cleavage removal benzyl groups.

参考文章(67)
Yoshio Nishimura, gem-Diamine 1-N-Iminosugars and Related Iminosugars, Candidate of Therapeutic Agents for Tumor Metastasis Current Topics in Medicinal Chemistry. ,vol. 3, pp. 575- 591 ,(2003) , 10.2174/1568026033452492
Norio Shibata, Satoshi Mizuta, Hiroyuki Kawai, Recent advances in enantioselective trifluoromethylation reactions Tetrahedron-asymmetry. ,vol. 19, pp. 2633- 2644 ,(2008) , 10.1016/J.TETASY.2008.11.011
Yoshikazu Tanaka, Junko Kato, Michinori Kohara, Mark S. Galinski, Antiviral effects of glycosylation and glucose trimming inhibitors on human parainfluenza virus type 3. Antiviral Research. ,vol. 72, pp. 1- 9 ,(2006) , 10.1016/J.ANTIVIRAL.2006.03.016
Kimberly A Watson, Edward P Mitchell, Louise N Johnson, Claire JF Bichard, Michael G Orchard, George WJ Fleet, Nikos G Oikonomakos, DD Leonidas, Jong Chan Son, None, Design of inhibitors of glycogen phosphorylase: a study of alpha- and beta-C-glucosides and 1-thio-beta-D-glucose compounds. Biochemistry. ,vol. 33, pp. 5745- 5758 ,(1994) , 10.1021/BI00185A011
Andrew Sutherland, Christine L. Willis, Synthesis of fluorinated amino acids Natural Product Reports. ,vol. 17, pp. 621- 631 ,(2000) , 10.1039/A707503K
Robert J. Nash, E. Arthur Bell, J. Michael Williams, 2-hydroxymethyl-3,4-dihydroxypyrrolidine in fruits of angylocalyx boutiqueanus Phytochemistry. ,vol. 24, pp. 1620- 1622 ,(1985) , 10.1016/S0031-9422(00)81084-5
Cheng-yi Chen, Danny Gauvreau, Francis Gosselin, Greg Hughes, Christian Nadeau, Ralph P. Volante, Paul D. O’Shea, A Practical Enantioselective Synthesis of Odanacatib, a Potent Cathepsin K Inhibitor, via Triflate Displacement of an α-Trifluoromethylbenzyl Triflate Journal of Organic Chemistry. ,vol. 74, pp. 1605- 1610 ,(2009) , 10.1021/JO8020314
Wei Zhang, Kasumi Sato, Atsushi Kato, Yue-Mei Jia, Xiang-Guo Hu, Francis X. Wilson, Renate van Well, Graeme Horne, George W. J. Fleet, Robert J. Nash, Chu-Yi Yu, Synthesis of fully substituted polyhydroxylated pyrrolizidines via Cope-House cyclization. Organic Letters. ,vol. 13, pp. 4414- 4417 ,(2011) , 10.1021/OL201749C
Gary L. Grunewald, Jian Lu, Kevin R. Criscione, Cosmas O. Okoro, Inhibitors of phenylethanolamine N-methyltransferase devoid of α2-adrenoceptor affinity Bioorganic & Medicinal Chemistry Letters. ,vol. 15, pp. 5319- 5323 ,(2005) , 10.1016/J.BMCL.2005.08.033