Development of a practical synthesis of a TORC1/2 inhibitor: A scalable application of memory of chirality

Organic Process Research and Development

Volumn 17, Issue 5, 2013, Pages 829-837

  Hicks, Frederick ^a   Hou, Yongquan ^a   Langston, Marianne ^a   McCarron, Ashley ^a   O'Brien, Erin ^a   Ito, Tatsuya ^b   Ma, Chunrong ^c   Matthews, Chris ^c   O'Bryan, Colin ^c   Provencal, David ^c   Zhao, Yuxin ^c   Huang, Jie ^d   Yang, Qiang ^d   Heyang, Li ^e   Johnson, Matthew ^e   Sitang, Yan ^e   Yuqiang, Liu ^e  

^a MILLENNIUM PHARMACEUTICALS INC   (United States)

^b TAKEDA PHARMACEUTICAL COMPANY LIMITED   (Japan)

^c Process Chemistry Gilead Sciences   (United States)

^d ALBANY MOLECULAR RESEARCH INC   (United States)

^e TEDA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BOND-FORMING STEP; ENANTIOMERIC EXCESS; MEMORY OF CHIRALITIES; PALLADIUM-CATALYZED; REDUCTIVE CYCLIZATION; RESEARCH AND DEVELOPMENT; ROUTE SELECTION; SCALABLE SYNTHESIS;

CYCLIZATION;

CHIRALITY;

EID: 84878056477     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op300330f     Document Type: Article

References (18)

1. Jacinto, E.; Hall, M. N. Nat. Rev. Mol. Cell. Biol. 2003, 4, 117
2. Hay, N.; Sonenberg, N. Genes Dev. 2004, 18, 1926
3. Wullschleger, S.; Loewith, R.; Hall, M. N. Cell 2006, 124, 471
4. Seeliger, H.; Guba, M.; Kleespies, A.; Jauch, K. W.; Bruns, C. J. Cancer Metastasis Rev. 2007, 26, 611
5. Smolewski, P. Anti-Cancer Drugs 2006, 17, 487
6. Zoncu, R.; Efeyan, A.; Sabatini, D. M. Nat. Rev. Mol. Cell. Biol. 2011, 12, 21
7. Agulnik, M. Cancer 2012, 118, 1486
8. Schenone, S.; Brullo, C.; Musumeci, F.; Radi, M.; Botta, M. Curr. Med. Chem. 2011, 18, 2995
9. Scorah, N.; Jin, B.; Dong, Q. PCT Int. Appl. WO/2011/025889 A1, 2011.
10. For a synthetic procedure for compound 9 see: Verheijen, J. C.; Zask, A.; Richard, D. J.; Kaplan, J. A.; Curran, K. J. PCT Int. Appl. WO/2010/120998 A1, 2010.
11. Yar, M.; McGarrigle, E. M.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2008, 47, 3784
12. Yar, M.; McGarrigle, E. M.; Aggarwal, V. K. Org. Lett. 2009, 11, 257
13. Brown, G. R.; Foubister, A. J.; Wright, B. J. Chem. Soc., Perkin Trans. 1 1985, 257
14. Kawabata, T.; Fuji, K. J. Synth. Org. Chem., Jpn. 2000, 58, 1095
15. Kawabata, T.; Matsuda, S.; Kawakami, S.; Monguchi, D.; Moriyama, K. J. Am. Chem. Soc. 2006, 128, 15394
16. For a review on memory of chirality see: Zhao, H.; Hsu, D. C.; Carlier, P. R. Synthesis 2005, 1
17. Deng, X.; Yang, Q.; Kwiatkowski, N.; Sim, T.; McDermott, U.; Settleman, J. E.; Lee, J. D.; Gray, N. S. ACS Med. Chem. Lett 2011, 2, 195
18. Baumeister, P.; Blaser, H. U.; Studer, M. Catal. Lett. 1997, 49, 219-222