Synthesis of valsartan via decarboxylative biaryl coupling

Journal of Organic Chemistry

Volumn 72, Issue 19, 2007, Pages 7473-7476

  Goossen, Lukas J ^a   Melzer, Bettina ^a  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYANOCARBOXYLIC ACID; ECOLOGICAL ADVANTAGES; ORGANOMETALLIC REAGENTS; STOICHIOMETRIC AMOUNTS;

BENZENE; BIOSYNTHESIS; CARBOXYLIC ACIDS; COPPER COMPOUNDS; ORGANOMETALLICS; STOICHIOMETRY;

PROTEINS;

1 BROMO (4 DIMETHOXYMETHYL)BENZENE; 1,10 PHENANTHROLINE; 2 CYANOCARBOXYLIC ACID; ANGIOTENSIN II ANTAGONIST; BENZENE DERIVATIVE; CARBOXYL GROUP; CARBOXYLIC ACID DERIVATIVE; CARBOXYLYASE; COPPER DERIVATIVE; LOSARTAN POTASSIUM; ORGANOMETALLIC COMPOUND; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG; VALSARTAN;

ARTICLE; CATALYST; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; QUANTUM YIELD; REACTION ANALYSIS; STOICHIOMETRY;

ANGIOTENSIN II TYPE 1 RECEPTOR BLOCKERS; BENZENE DERIVATIVES; TETRAZOLES; VALINE;

EID: 34548747604     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701391q     Document Type: Article

References (21)

1. U.S. Department of Health and Human Services; National Heart, Lung, and Blood Institute; National High Blood Pressure Education Program, NIH Publication No. 03-5233, December 2003.
2. (a) Duncia, J.; Chiu, A.; Carini, D.; Georgory, G.; Johnson, A.; Price, W.; Wells, G.; Wong, P.; Calabrese, J.; Timmermans, P. J. Med. Chem. 1990, 33, 1312-1329.
3. (b) Carini, D.; Duncia, J.; Aldrich, P.; Chiu, A.; Johnson, A.; Pierce, M.; Price, W.; Santella, J., III; Wells, G.; Wexler, R.; Wong, P.; Yoo, S. E.; Timmermans, P. J. Med. Chem. 1991, 34, 2525-2547.
4. For sales figures, see: Novartis Annual Report 2006; Novartis International AG: Basel, Switzerland, 2007.
5. For published syntheses, see: (a) Bühlmayer, P.; Ostermayer, F.; Schmidlin, T. Eur. Pat. Appl. EP443983, 1991.
6. (b) Bühlmayer, P.; Ostermayer, F.; Schmidlin, T. U.S. Patent 5,339,578, 1995.
7. (c) Bühlmayer, P.; Furet, P.; Criscione, L.; de Gasparo, M.; Whitebread, S.; Schmidlin, T.; Lattmann, R.; Wood, J. Bioorg. Med. Chem. Lett. 1994, 4, 29-34.
8. For clinical trial results, see: (a) Novartis Pharma Schweiz, AG. Health & Science 2005, 2, 8-9.
9. (b) McMurry, J.; Solomon, S.; Pieper, K.; Reed, S.; Rouleau, J.; Velazquez, E.; White, H.; Howlett, J.; Swedberg, K.; Maggioni, A.; Køber, L.; Van de Werf, F.; Califf, R.; Pfeffer, M. J. Am. Coll. Cardiol. 2006, 47, 726-733.
10. (a) Negishi, E.; King, A. O.; Okukado, N. J. Org. Chem. 1977, 42, 1821-1823.
11. (b) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442-4489.
12. Fanta, P. E. Chem. Rev. 1964, 64, 613-632.
13. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
14. For state-of-the-art Suzuki couplings, see: (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
15. (b) Kristensen, J.; Lysén, M.; Vedsø, P.; Begtrup, M. Org. Lett. 2001, 3, 1435-1437.
16. (a) Goossen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662-664.
17. (b) Goossen, L. J.; Rodríguez, N.; Melzer, B.; Linder, C.; Deng, G.; Levy, L. M. J. Am. Chem. Soc. 2007, 12, 4824-4833.
18. (c) Goossen, L. J.; Thiel, W. R.; Rodríguez, N.; Linder, C.; Melzer, B. Adv. Synth. Catal., in press.
19. (a) Tanaka, D.; Romeril, S. P.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 10323-10333.
20. (b) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147-1152.
21. (c) Forgione, P.; Brochu, M.-C.; St-Onge, M.; Thesen, K. H.; Bailey, M. D.; Bilodeau, F. J. Am. Chem. Soc. 2006, 128, 11350-11351.