Erratum: Synthesis of Prostaglandin Analogues, Latanoprost and Bimatoprost, Using Organocatalysis via a Key Bicyclic Enal Intermediate (Org. Lett. (2015) 17:3 (504−507) DOI: 10.1021/ol503520f);Synthesis of prostaglandin analogues, latanoprost and bimatoprost, using organocatalysis via a key bicyclic enal intermediate

Organic Letters

Volumn 17, Issue 3, 2015, Pages 504-507

  Prévost, Sébastien ^a   Thai, Karen ^a   Schützenmeister, Nina ^a   Coulthard, Graeme ^a   Erb, William ^a   Aggarwal, Varinder K ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYBUTANAL; ALDEHYDE; AMIDE; BIMATOPROST; CLOPROSTENOL; LATANOPROST; PROSTAGLANDIN DERIVATIVE; PROSTAGLANDIN F; PROSTAGLANDIN F2 ALPHA;

ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALDEHYDES; AMIDES; CLOPROSTENOL; DINOPROST; MOLECULAR STRUCTURE; PROSTAGLANDINS F, SYNTHETIC; PROSTAGLANDINS, SYNTHETIC;

EID: 84922594721     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.3c02579     Document Type: Erratum

References (50)

1. Bindra, J. S.; Bindra, R. Prostaglandin Synthesis; Academic Press: 1977.
2. Funk, C. D. Science 2001, 294, 1871
3. Das, S.; Chandrasekhar, S.; Yadav, J. S.; Grée, R. Chem. Rev. 2007, 107, 3286
4. Dams, I.; Wasyluk, J.; Prost, M.; Kutner, A. Prostaglandins Other Lipid Mediators 2013, 109
5. Collins, P. W.; Djuric, S. W. Chem. Rev. 1993, 93, 1533
6. Nair, S. K.; Henegar, K. E. Latanoprost (Xalatan): A Prostanoid FP Agonist for Glaucoma. In Modern Drug Synthesis; Li, J. J.; Johnson, D. S., Eds.; John Wiley & Sons, Inc.: Hoboken, NJ, USA, 2010; pp 329-338.
7. Full-year results for 2010 were reported by Pfizer: http://www.pfizer.com/files/investors/presentations/q4performance-020111.pdf.
8. Noecker, R. S.; Dirks, M. S.; Choplin, N. T.; Bernstein, P.; Batoosingh, A. L.; Witcup, S. M. Am. J. Ophthalmol. 2003, 135, 55
9. Simmons, S. T.; Dirks, M. S.; Noecker, R. J. Adv. Ther. 2004, 21, 754
10. Dams, I.; Chodyński, M.; Krupa, M.; Pietraszek, A.; Zezula, M.; Cmoch, P.; Kosińska, M.; Kutner, A. Chirality 2013, 25, 170
11. Fagien, S. Clin. Cosmet. Invest. Dermatol. 2010, 3, 39
12. Corey, E. J.; Winshenker, N. M.; Schaaf, T. K.; Huber, W. J. Am. Chem. Soc. 1969, 91, 5675
13. Obadalová, I.; Pilarčík, T.; Slavíková, M.; Hájíček, J. Chirality 2005, 109
14. Martynow, J. G.; Józwik, J.; Szelejewski, W.; Achmatowicz, O.; Kutner, A.; Wis̈niewski, K.; Winiarski, J.; Zegrock-Stendel, O.; Golëbiewski, P. Eur. J. Org. Chem. 2007, 689
15. Zanoni, G.; DAlfonso, A.; Porta, A.; Feliciani, L.; Nolan, S. P.; Vidari, G. Tetrahedron 2010, 66, 7472
16. Harikrishna, M.; Mohan, H. R.; Dubey, P. K.; Shankar, M.; Subbaraju, G. V. Asian J. Chem. 2011, 23, 3121
17. Mariani, E.; Orru, G.; Montorsi, M.; Andriolo, E.; Bandini, M.; Contento, M.; Tolomelli, A. Eur. Pat. Appl. (2012) EP 2495235 A1 20120905.
18. Contente, M. L.; Zambelli, P.; Galafassi, S.; Tamborini, L.; Pinto, A.; Conti, P.; Molinari, F.; Romano, D. J. Mol. Catal. B: Enzym. DOI: 10.1016/j.molcatb.2014.05.022.
19. Ham, W.-H.; Oh, C.-Y.; Kim, Y.-H.; Lee, Y.-S.; Lee, K.-Y. World Patent Application, No. 02/090324A1, 2002.
20. Obadalová, I.; Pilarčik, T.; Slavíková, M.; Hájíček, J. Chirality 2005, 17, 109
21. Dominic De, S.; Albert, M.; Sturm, H. World Patent Application, No. 2009153206A2, 2009.
22. Sandoz AG European Patent Application, No. EP2135860A1, 2009.
23. Harikrishna, M.; Rama Mohan, H.; Dubey, P. K.; Shankar, M.; Subbaraju, G. V. Synth. Commun. 2012, 42, 1288
24. Dams, I.; Chodyński, M.; Krupa, M.; Pietraszek, A.; Zezula, M.; Cmoch, P.; Kosińska, M.; Kutner, A. Chirality 2013, 25, 170
25. Coulthard, G.; Erb, W.; Aggarwal, V. K. Nature 2012, 489, 278
26. Hayashi, Y.; Umemiya, S. Angew. Chem., Int. Ed. 2013, 52, 3450
27. Aggarwal, V. K.; Coulthard, G.; Erb, W. PCT Int. Appl. (2013) WO 2013/186550 A1.
28. Hoover, J. M.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 16901
29. Hoover, J. M.; Ryland, B. L.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 2357
30. Kim, I. S.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14891
31. Hassan, A.; Lu, Y.; Krische, M. J. Org. Lett. 2009, 11, 3112
32. Victor Paul Raj, I.; Sudalai, A. Tetrahedron Lett. 2008, 49, 2646
33. Fernández, E.; Pietruszka, J.; Frey, W. J. Org. Chem. 2010, 75, 5580
34. Denmark, S. E.; Heemstra, J. R., Jr. J. Am. Chem. Soc. 2005, 128, 1038
35. Denmark, S. E.; Wilson, T. W. Angew. Chem., Int. Ed. 2012, 51, 3236
36. N͡nez, M. T.; Martín, V. S. J. Org. Chem. 1990, 55, 1928
37. Peng, F.; Hall, D. G. Tetrahedron Lett. 2007, 48, 3305
38. Bovall, D.; López, F.; Sasaki, H.; Frantz, D.; Carreira, E. M. Org. Lett. 2000, 2, 4233
39. Frantz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806
40. Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 937
41. Ramos Tombo, G. M.; Didier, E.; Loubinoux, B. Synlett 1990, 547
42. Tan, L.; Chen, C.; Tillyer, R. D.; Grabowski, E. J. J.; Reider, P. J. Angew. Chem., Int. Ed. 1999, 38, 711
43. Li, Z.; Upadhyay, V.; DeCamp, A. E.; DiMichele, L.; Reider, P. J. Synthesis 1999, 1453
44. Hale, K. J.; Grabski, M.; Manaviazar, S.; Maczka, M. Org. Lett. 2014, 16, 1164
45. Hale, K. J.; Hatakeyama, S.; Urabe, F.; Ishihara, J.; Manaviazar, S.; Grabski, M.; Maczka, M. Org. Lett. 2014, 16, 3536
46. Clark, D. A.; Kulkarni, A. A.; Kalbarczyk, K.; Schertzer, B.; Diver, S. T. J. Am. Chem. Soc. 2006, 128, 15632
47. World International Application, No. WO2005058812A2, 2005.
48. Kiyotsuka, Y.; Katayama, Y.; Acharya, H. P.; Hyodo, T.; Kobayashi, Y. J. Org. Chem. 2008, 74, 1939
49. Makida, Y.; Ohmiya, H.; Sawamura, M. Angew. Chem., Int. Ed. 2012, 51, 4122
50. Lipshutz, B. H.; Kozlowski, J. A.; Parker, D. A.; Nguyen, S. L.; McCarthy, K. E. J. Organomet. Chem. 1985, 285, 437