Erratum: Origins of regioselectivity in the fischer indole synthesis of a selective androgen receptor modulator (Journal of Organic Chemistry (2017) 82:11 (5904-5909) DOI: 10.1021/acs.joc.7b00878);Origins of Regioselectivity in the Fischer Indole Synthesis of a Selective Androgen Receptor Modulator

Journal of Organic Chemistry

Volumn 82, Issue 11, 2017, Pages 5904-5909

  Noey, Elizabeth L ^a   Yang, Zhongyue ^a   Li, Yanwei ^a   Yu, Hannah ^b   Richey, Rachel N ^b   Merritt, Jeremy M ^b   Kjell, Douglas P ^b   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISEASES; MOLECULAR DYNAMICS; POLYCYCLIC AROMATIC HYDROCARBONS; REACTION INTERMEDIATES; REACTION KINETICS;

ANDROGEN RECEPTORS; DECOMPOSITION PRODUCTS; DIFFERENT MECHANISMS; ELECTRONWITHDRAWING; FISCHER INDOLE SYNTHESIS; MOLECULAR DYNAMICS SIMULATIONS; ORGANIC CHEMISTRY; SIGMATROPIC REARRANGEMENTS;

REGIOSELECTIVITY;

INDOLE; SELECTIVE ANDROGEN RECEPTOR MODULATOR; ANDROGEN RECEPTOR; AR PROTEIN, HUMAN; CARBAMIC ACID DERIVATIVE; INDOLE DERIVATIVE; LY2452473;

ARTICLE; CATALYSIS; DECOMPOSITION; DRUG SYNTHESIS; ISOMER; MOLECULAR DYNAMICS; REACTION ANALYSIS; REGIOSELECTIVITY; CHEMISTRY; CONFORMATION; HUMAN; MALE; METABOLISM; PROSTATE TUMOR; QUANTUM THEORY; STEREOISOMERISM; SYNTHESIS; THERMODYNAMICS;

CARBAMATES; HUMANS; INDOLES; MALE; MOLECULAR CONFORMATION; MOLECULAR DYNAMICS SIMULATION; PROSTATIC NEOPLASMS; QUANTUM THEORY; RECEPTORS, ANDROGEN; STEREOISOMERISM; THERMODYNAMICS;

EID: 85020001455     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.7b02416     Document Type: Erratum

References (25)

1. Indole Ring Synthesis-From Natural Products to Drug Discovery; Gribble, G.W., Ed.; Wiley, 2016.
2. Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875-2911 10.1021/cr0505270
3. Fischer, E.; Jourdan, F. Ber. Dtsch. Chem. Ges. 1883, 16, 2241-2245 10.1002/cber.188301602141
4. Fischer, E.; Hess, O. Ber. Dtsch. Chem. Ges. 1884, 17, 559-568 10.1002/cber.188401701155
5. Fales, K. R.; Green, J. E.; Jadhav, P. K.; Matthews, D. P.; Neel, D. A.; Smith, E. C. R.; Tetrahydrocarbazole derivatives useful as androgen receptor modulators, WO2007002181A2, Jan 4, 2007.
6. Jadhav, P. K.; Krishnan, V.; Kim, E. J., Tetrahydrocyclopenta[b]indole androgen receptor modulators. WO2009140448A1, Nov 19, 2009.
7. Benson, C. T., Treatment of Androgen Deprivation Therapy Associated Symptoms. WO 2016040234Al, Sep 8, 2015.
8. Nguyen, P. L.; Alibhai, S. M.; Basaria, S.; D'Amico, A. V.; Kantoff, P. W.; Keating, N. L.; Penson, D. F.; Rosario, D. J.; Tombal, B.; Smith, M. R. Eur. Urol. 2015, 67, 825-836 10.1016/j.eururo.2014.07.010
9. Krupski, T. L.; Smith, M. R.; Chan Lee, W.; Pashos, C. L.; Brandman, J.; Wang, Q.; Botteman, M.; Litwin, M. S. Cancer 2004, 101, 541-549 10.1002/cncr.20388
10. Wilke, D. R.; Parker, C.; Andonowski, A.; Tsuji, D.; Catton, C.; Gospodarowicz, M.; Warde, P. BJU Int. 2006, 97, 963-968 10.1111/j.1464-410X.2006.06066.x
11. Çelebi-Ölçüm, N.; Boal, B. W.; Huters, A. D.; Garg, N. K.; Houk, K. N. J. Am. Chem. Soc. 2011, 133, 5752-5755 10.1021/ja201035b
12. Ess, D. H.; Wheeler, S. E.; Iafe, R. G.; Xu, L.; Çelebi- Ölçüm, N.; Houk, K. N. Angew. Chem., Int. Ed. 2008, 47, 7592-7601 10.1002/anie.200800918
13. Thomas, J. B.; Waas, J. R.; Harmata, M.; Singleton, D. J. Am. Chem. Soc. 2008, 130, 14544-14555 10.1021/ja802577v
14. Martin-Somer, A.; Yanez, M.; Hase, W. L.; Gaigeot, M.-P.; Spezia, R. J. Chem. Theory Comput. 2016, 12, 974-982 10.1021/acs.jctc.5b01135
15. Gaussian 09, revision D.01: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonneerg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, M. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian, Inc., Wallingford, CT, 2009.
16. Ribeiro, R. F.; Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2011, 115, 14556-14562 10.1021/jp205508z
17. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241 10.1007/s00214-007-0310-x
18. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157-167 10.1021/ar700111a
19. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378-6396 10.1021/jp810292n
20. Yang, Z.; Doubleday, C.; Houk, K. N. J. Chem. Theory Comput. 2015, 11, 5606-5612 10.1021/acs.jctc.5b01029
21. Yang, Z.; Yu, P.; Houk, K. N. J. Am. Chem. Soc. 2016, 138, 4237-4242 10.1021/jacs.6b01028
22. Doubleday, C.; Bolton, K.; Hase, W. L. J. Phys. Chem. A 1998, 102, 3648-3658 10.1021/jp973273y
23. Black, K.; Liu, P.; Xu, L.; Doubleday, C.; Houk, K. N. Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 12860-12865 10.1073/pnas.1209316109
24. Bunker, D. L.; Hase, W. L. J. Chem. Phys. 1973, 59, 4621-4632 10.1063/1.1680672
25. Oyola, Y.; Singleton, D. A. J. Am. Chem. Soc. 2009, 131, 3130-3131 10.1021/ja807666d