Expanding the azaspiro[3.3]heptane family: Synthesis of novel highly functionalized building blocks

Organic Letters

Volumn 14, Issue 1, 2012, Pages 66-69

  Burkhard, Johannes A ^a   Guérot, Carine ^a,b   Knust, Henner ^b   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; HEPTANE; HETEROCYCLIC COMPOUND; OXETANE; SPIRO COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AZA COMPOUNDS; ETHERS, CYCLIC; HEPTANES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SPIRO COMPOUNDS;

EID: 84855493475     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2028459     Document Type: Article

References (26)

1. Wuitschik, G.; Carreira, E. M.; Wagner, B.; Fischer, H.; Parrilla, I.; Schuler, F.; Rogers-Evans, M.; Müller, K. J. Med. Chem. 2010, 53, 3227-3246
2. Burkhard, J. A.; Wuitschik, G.; Rogers-Evans, M.; Müller, K.; Carreira, E. M. Angew. Chem., Int. Ed. 2010, 49, 9052-9067
3. Burkhard, J. A.; Wagner, B.; Fischer, H.; Schuler, F.; Müller, K.; Carreira, E. M. Angew. Chem., Int. Ed. 2010, 49, 3524-3527
4. Burkhard, J. A.; Guérot, C.; Knust, H.; Rogers-Evans, M.; Carreira, E. M. Org. Lett. 2010, 12, 1944-1947
5. Guérot, C.; Tchitchanov, B. H.; Knust, H.; Carreira, E. M. Org. Lett. 2011, 13, 780-783
6. For an insightful account on unusual molecular scaffolds in drug design, see: Marson, C. M. Chem. Soc. Rev. 2011, 40, 5514-5533
7. Prepared in three steps from tribromopentaerythritol. For details, see ref 1c and Burkhard, J.; Carreira, E. M. Org. Lett. 2008, 10, 3525-3526
8. Couladouros, E. A.; Vidali, V. P. Chem.-Eur. J. 2004, 10, 3822-3835
9. Searles, S.; Nickerson, R. G.; Witsiepe, W. K. J. Org. Chem. 1960, 24, 1839-1844
10. Borg, G.; Chino, M.; Ellman, J. A. Tetrahedron Lett. 2001, 42, 1433-1435
11. Luo, Y.-C.; Zhang, H.-H.; Xu, P.-F. Synlett 2009, 833-837
12. Luo, Y.-C.; Zhang, H.-H.; Liu, Y.-Z.; Cheng, R.-L.; Xu, P.-F. Tetrahedron: Asymmetry 2009, 20, 1174-1180
13. 2: Sun, P.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1997, 62, 8604-8608
14. Dejaegher, Y.; Kuz'menok, N. M.; Zvonok, A. M.; De Kimpe, N. Chem. Rev. 2002, 102, 29-60
15. Brandi, A.; Cicchi, S.; Cordero, F. M. Chem. Rev. 2008, 108, 3988-4035
16. Ye, L.; He, W.; Zhang, L. Angew. Chem., Int. Ed. 2011, 50, 3236-3239
17. Ye, L.; He, W.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 8550-8551
18. Baker, R. K.; Bao, J.; Miao, S.; Rupprecht, K. M. (Merck & Co., Inc.), WO 2005/000809, 2005.
19. Ojima, I.; Zhao, M.; Yamato, T.; Nakahashi, K.; Yamashita, M.; Abe, R. J. Org. Chem. 1991, 56, 5263-5277
20. Jackson, M.; Mander, L.; Spotswood, T. Aust. J. Chem. 1983, 36, 779-788
21. Takahashi, Y.; Yamashita, H.; Kobayashi, S.; Ohno, M. Chem. Pharm. Bull. 1986, 34, 2732-2742
22. Yamashita, H.; Minami, N.; Sakakibara, K.; Kobayashi, S.; Ohno, M. Chem. Pharm. Bull. 1988, 36, 469-480
23. Folmer, J. J.; Acero, C.; Thai, D. L.; Rapoport, H. J. Org. Chem. 1998, 63, 8170-8182
24. Schneider, G.; Neidhart, W.; Giller, T.; Schmid, G. Angew. Chem., Int. Ed. 1999, 38, 2894-2896
25. Schneider, G.; Schneider, P.; Renner, S. QSAR Comb. Sci. 2006, 25, 1162-1171
26. Schneider, G.; Fechner, U. Nat. Rev. Drug Discov. 2005, 4, 649-663