Access the full text.
Sign up today, get DeepDyve free for 14 days.
Loading next page...
/lp/wiley/synthesis-of-1-3-5-trisubstituted-4-tert-butyl-2-5-5-difluoro-2-2-QZCPLKxXaY
References (35)
-
Xiao Chen, Charles Goodhue, jin-quan yu (2006)
Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids: two distinct C-H activation pathways.Journal of the American Chemical Society, 128 39
-
Ichiro Moritanl, Y. Fujiwara (1967)
Aromatic substitution of styrene-palladium chloride complexTetrahedron Letters, 8
-
M. Miyasaka, K. Hirano, T. Satoh, M. Miura (2010)
Palladium-catalyzed direct oxidative alkenylation of azoles.The Journal of organic chemistry, 75 15
-
Xingang Zhang, S. Fan, Chun-Yang He, X. Wan, Qiao‐Qiao Min, J. Yang, Zhong-Xing Jiang (2010)
Pd(OAc)(2) catalyzed olefination of highly electron-deficient perfluoroarenes.Journal of the American Chemical Society, 132 13
-
Roman Goikhman, Teresa Jacques, D. Sames (2009)
C-H bonds as ubiquitous functionality: a general approach to complex arylated pyrazoles via sequential regioselective C-arylation and N-alkylation enabled by SEM-group transposition.Journal of the American Chemical Society, 131 8
-
F. Bennett, D. Knight, G. Fenton (1988)
Chiral synthons for the elaboration of mevinic acid analoguesTetrahedron Letters, 29
-
J. Roger, Aditya Gottumukkala, H. Doucet (2010)
Palladium‐Catalyzed C3 or C4 Direct Arylation of Heteroaromatic Compounds with Aryl Halides by CH Bond ActivationChemCatChem, 2
-
Julia Castro, J. Coterón, M. Fraile, Silvestre Garcı́a-Ochoa, F. Heras, Antonio Martı́n-Cuesta (2002)
A new synthesis of 3,5-dihydroxy-7-(1-pyrrolyl)-6-heptenoic acids, a family of HMGCoA reductase inhibitors with antifungal activityTetrahedron Letters, 43
-
J. Pfefferkorn, Yun-Song Song, Kuai-lin Sun, S. Miller, B. Trivedi, Chulho Choi, R. Sorenson, L. Bratton, P. Unangst, S. Larsen, T. Poel, Xue-min Cheng, Chitase Lee, Noe Erasga, B. Auerbach, Valerie Askew, L. Dillon, J. Hanselman, Zhiwu Lin, G. Lu, A. Robertson, Karl Olsen, T. Mertz, C. Sekerke, A. Pavlovsky, M. Harris, G. Bainbridge, N. Caspers, Huifen Chen, M. Eberstadt (2007)
Design and synthesis of hepatoselective, pyrrole-based HMG-CoA reductase inhibitors.Bioorganic & medicinal chemistry letters, 17 16
-
Mikio Suzuki, H. Iwasaki, Y. Fujikawa, M. Sakashita, M. Kitahara, R. Sakoda (2001)
Synthesis and biological evaluations of condensed pyridine and condensed pyrimidine-based HMG-CoA reductase inhibitors.Bioorganic & medicinal chemistry letters, 11 10
-
M. Tozer, Timothée Herpin (1996)
Methods for the synthesis of gem-difluoromethylene compoundsTetrahedron, 52
-
Ben Chappell, Nathan Dedman, S. Wheeler (2011)
Studies on the palladium-catalysed direct alkenylation of 1,2-azolesTetrahedron Letters, 52
-
Yanghui Zhang, Bing‐Feng Shi, jin-quan yu (2009)
Pd(II)-catalyzed olefination of electron-deficient arenes using 2,6-dialkylpyridine ligands.Journal of the American Chemical Society, 131 14
-
J. Pfefferkorn, Chulho Choi, S. Larsen, B. Auerbach, R. Hutchings, W. Park, Valerie Askew, L. Dillon, J. Hanselman, Zhiwu Lin, G. Lu, A. Robertson, C. Sekerke, M. Harris, A. Pavlovsky, G. Bainbridge, N. Caspers, M. Kowala, B. Tait (2008)
Substituted pyrazoles as hepatoselective HMG-CoA reductase inhibitors: discovery of (3R,5R)-7-[2-(4-fluoro-phenyl)-4-isopropyl-5-(4-methyl-benzylcarbamoyl)-2H-pyrazol-3-yl]-3,5-dihydroxyheptanoic acid (PF-3052334) as a candidate for the treatment of hypercholesterolemia.Journal of medicinal chemistry, 51 1
-
S. Grundy (1997)
Primary prevention of coronary heart disease: role of cholesterol control in the United StatesJournal of Internal Medicine, 241
-
D. Sliskovic, B. Roth, M. Wilson, M. Hoefle, R. Newton (1990)
Inhibitors of cholesterol biosynthesis. 2. 1,3,5-trisubstituted [2-(tetrahydro-4-hydroxy-2-oxopyran-6-yl)ethyl]pyrazoles.Journal of medicinal chemistry, 33 1
-
E. Beck, N. Grimster, R. Hatley, M. Gaunt (2006)
Mild aerobic oxidative palladium (II) catalyzed C-H bond functionalization: regioselective and switchable C-H alkenylation and annulation of pyrroles.Journal of the American Chemical Society, 128 8
-
E. Ferreira, B. Stoltz (2003)
Catalytic C-H bond functionalization with palladiumII: aerobic oxidative annulations of indoles.Journal of the American Chemical Society, 125 32
-
R. Sarver, Elizabeth Bills, G. Bolton, L. Bratton, N. Caspers, J. Dunbar, M. Harris, R. Hutchings, R. Kennedy, S. Larsen, A. Pavlovsky, J. Pfefferkorn, G. Bainbridge (2008)
Thermodynamic and structure guided design of statin based inhibitors of 3-hydroxy-3-methylglutaryl coenzyme A reductase.Journal of medicinal chemistry, 51 13
-
R. Giri, N. Maugel, Jiao Li, Dong-Hui Wang, Steven Breazzano, L. Saunders, jin-quan yu (2007)
Palladium-catalyzed methylation and arylation of sp2 and sp3 C-H bonds in simple carboxylic acids.Journal of the American Chemical Society, 129 12
-
S. Jeon, J. Choi, B. Kim, I. Jeong (2007)
Synthesis of novel 1,4,5-trisubstituted 3-trifluoromethylpyrazoles via microwave-assisted Stille coupling reactionsJournal of Fluorine Chemistry, 128
-
Xiaoguang Wang, Xiang Fang, Hongyuan Xiao, Yan-bai Yin, Huimin Xia, Fan-hong Wu (2012)
Synthesis of γ,γ-difluoro-β-hydroxy-δ-lactones as new precursors of HMG-CoA reductase inhibitorJournal of Fluorine Chemistry, 133
-
B. Roth, D. Ortwine, M. Hoefle, C. Stratton, D. Sliskovic, M. Wilson, R. Newton (1990)
Inhibitors of cholesterol biosynthesis. 1. trans-6-(2-pyrrol-1-ylethyl)-4-hydroxypyran-2-ones, a novel series of HMG-CoA reductase inhibitors. 1. Effects of structural modifications at the 2- and 5-positions of the pyrrole nucleus.Journal of medicinal chemistry, 33 1
-
H. Dai, A. Stepan, M. Plummer, Yanghui Zhang, jin-quan yu (2011)
Divergent C-H functionalizations directed by sulfonamide pharmacophores: late-stage diversification as a tool for drug discovery.Journal of the American Chemical Society, 133 18
-
D. Bowles, D. Boyles, Chulho Choi, J. Pfefferkorn, S. Schuyler, E. Hessler (2011)
Development of an Early Enabling Synthesis for PF-03052334-02: A Novel Hepatoselective HMG-CoA Reductase InhibitorOrganic Process Research & Development, 15
-
D. Sliskovic, J. Picard, W. Roark, B. Roth, E. Ferguson, B. Krause, R. Newton, C. Sekerke, M. Shaw (1991)
Inhibitors of cholesterol biosynthesis. 4. trans-6-[2-(substituted-quinolinyl)ethenyl/ethyl]tetrahydro-4-hydroxy-2 H-pyran-2-ones, a novel series of HMG-CoA reductase inhibitors.Journal of medicinal chemistry, 34 1
-
M. Watanabe, H. Koike, T. Ishiba, T. Okada, S. Seo, K. Hirai (1997)
Synthesis and biological activity of methanesulfonamide pyrimidine- and N-methanesulfonyl pyrrole-substituted 3,5-dihydroxy-6-heptenoates, a novel series of HMG-CoA reductase inhibitors.Bioorganic & medicinal chemistry, 5 2
-
Sunliang Cui, L. Wojtas, J. Antilla (2011)
Pd-catalyzed C4-olefination of oxazoles via C-H bond activation: divergent synthesis of functionalized amino alcohol and amino acid derivatives.Organic letters, 13 19
-
Junliang Wu, Xiuling Cui, Lian‐Shan Chen, Guojie Jiang, Yangjie Wu (2009)
Palladium-catalyzed alkenylation of quinoline-N-oxides via C-H activation under external-oxidant-free conditions.Journal of the American Chemical Society, 131 39
-
Mikio Suzuki, Hiroshi Iwasaki, Y. Fujikawa, Masaki Kitahara, Mitsuaki Sakashita, Ryozo Sakoda (2001)
Synthesis and biological evaluations of quinoline-based HMG-CoA reductase inhibitors.Bioorganic & medicinal chemistry, 9 10
-
Chengguo Jia, Dongguo Piao, J. Oyamada, Wenjun Lu, T. Kitamura, Y. Fujiwara (2000)
Efficient activation of aromatic C-H bonds for addition to C-C multiple bondsScience, 287 5460
-
Saleem Ahmad, C. Madsen, P. Stein, E. Janovitz, Christine Huang, K. Ngu, S. Bisaha, L. Kennedy, Bang-Chi Chen, R. Zhao, Doree Sitkoff, H. Monshizadegan, Xiaohong Yin, Carol Ryan, Rongan Zhang, M. Giancarli, E. Bird, Ming Chang, Xing Chen, R. Setters, D. Search, Shaobin Zhuang, V. Nguyen-Tran, C. Cuff, T. Harrity, Celia Darienzo, Tonghui Li, R. Reeves, M. Blanar, J. Barrish, R. Zahler, J. Robl (2008)
(3R,5S,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(methyl(1-methyl-1h-1,2,4-triazol-5-yl)amino)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoic acid (BMS-644950): a rationally designed orally efficacious 3-hydroxy-3-methylglutaryl coenzyme-a reductase inhibitor with reduced myotoxicity potential.Journal of medicinal chemistry, 51 9
-
D. Sliskovic, C. Blankley, B. Krause, R. Newton, J. Picard, W. Roark, B. Roth, C. Sekerke, M. Shaw, R. Stanfield (1992)
Inhibitors of cholesterol biosynthesis. 6. trans-6-[2-(2-N-heteroaryl-3,5-disubstituted- pyrazol-4-yl)ethyl/ethenyl]tetrahydro-4-hydroxy-2H-pyran-2-ones.Journal of medicinal chemistry, 35 11
-
L. Bratton, B. Auerbach, Chulho Choi, L. Dillon, J. Hanselman, S. Larsen, G. Lu, Karl Olsen, J. Pfefferkorn, A. Robertson, C. Sekerke, B. Trivedi, P. Unangst (2007)
Discovery of pyrrole-based hepatoselective ligands as potent inhibitors of HMG-CoA reductase.Bioorganic & medicinal chemistry, 15 16
-
S. Cho, S. Hwang, Sukbok Chang (2008)
Palladium-catalyzed C-H functionalization of pyridine N-oxides: highly selective alkenylation and direct arylation with unactivated arenes.Journal of the American Chemical Society, 130 29
- Publisher
- Wiley
- Copyright
- Copyright © 2012 Wiley Subscription Services, Inc., A Wiley Company
- ISSN
- 1001-604X
- eISSN
- 1614-7065
- DOI
- 10.1002/cjoc.201201100
- Publisher site
- See Article on Publisher Site
Abstract
The gem‐difluoromethylenated acetonide 2 was efficiently synthesized as new precursor of HMG‐CoA reductase inhibitor. Straightforward olefination via Pd‐catalyzed C4‐H activation of 1,3,5‐trisubstituted pyrazoles 1 was proceeded smoothly in the presence of Pd(OAc)2 and AgCO3. This protocol has merits in terms of the improved atomic economy and prevention from the generation of by‐products.
Journal
Chinese Journal of Chemistry – Wiley
Published: Dec 1, 2012
Keywords: ; ; ;