Stereoselective synthesis of 3-aminoindan-1-ones and subsequent incorporation into HIV-1 protease inhibitors

Journal of Organic Chemistry

Volumn 71, Issue 3, 2006, Pages 1265-1268

  Arefalk, Anna ^a   Wannberg, Johan ^a   Larhed, Mats ^a   Hallberg, Anders ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITION; ENZYMES; ETHERS; GLYCOLS; KETONES; SOLVENTS; VIRUSES;

3-AMINOINDAN-1-ONES; ETHYLENE GLYCOL VINYL; HIV-1 PROTEASE INHIBITORS; SALICYLIC SULFINYL IMINES;

SYNTHESIS (CHEMICAL);

2,3 DIMETHYLNAPHTHALENE; 3 AMINOINDAN 1 ONE; ACETONITRILE; CITRIC ACID; ETHYLENE GLYCOL; IMINE; INDANONE DERIVATIVE; INDINAVIR; IODIDE; LEWIS ACID; NAPHTHALENE DERIVATIVE; PALLADIUM; PROTEINASE INHIBITOR; SALICYLALDEHYDE; SULFINAMIDE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; VINYL DERIVATIVE; ZINC;

ANNULATION REACTION; ARTICLE; CHROMATOGRAPHY; DIASTEREOISOMER; DRUG SYNTHESIS; HECK REACTION; HUMAN IMMUNODEFICIENCY VIRUS 1; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; RING OPENING; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

HIV PROTEASE INHIBITORS; IMINES; INDANS; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFONES;

EID: 32144454169     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0521504     Document Type: Article

References (23)

1. Ersmark, K.; Feierberg, I.; Bjelic, S.; Hamelink, E.; Hackett, F.; Blackman, M. J.; Hulten, J.; Samuelsson, B.; Qvist, J.; Hallberg, A. J. Med. Chem. 2004, 47, 110-122.
2. Vacca, J. P.; Dorsey, B. D.; Schleif, W. A.; Levin, R. B.; McDaniel, S. L.; Darke, P. L.; Zugay, J.; Quintero, J. C.; Blahy, O. M.; Roth, E. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 4096-4100.
3. Lyle, T. A.; Wiscount, C. M.; Guare, J. P.; Thompson, W. J.; Anderson, P. S.; Darke, P. L.; Zugay, J. A.; Emini, E. A.; Schleif, W. A.; Quintero, J. C.; Dixon, R. A. F.; Sigal, I. S.; Huff, J. R. J. Med. Chem. 1991, 34, 1228-1230.
4. Alterman, M.; Andersson, H. O.; Garg, N.; Ahlsen, G.; Lövgren, S.; Classon, B.; Danielson, U. H.; Kvarnström, I.; Vrang, L.; Unge, T.; Samuelsson, B.; Hallberg, A. J. Med. Chem. 1999, 42, 3835-3844.
5. Arefalk, A.; Larhed, M.; Hallberg, A. J. Org. Chem. 2005, 70, 938-942.
6. (a) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984-995.
7. (b) Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 60, 8003-8030.
8. (c) Tang, T. P.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772-8778.
9. (d) Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268-269.
10. (e) Jacobsen M. F.; Skrydstrup, T. J. Org. Chem. 2003, 68, 7112-7114.
11. (f) Aggarwal, V. K.; Castro, A. M. M.; Mereu, A.; Adams, H. Tetrahedron Lett. 2002, 43, 1577-1581.
12. (g) Nemoto, H.; Ma, R.; Moriguchi, H.; Suzuki, I.; Shibuya, M. J. Organomet. Chem. 2000, 611, 445-448.
13. (h) Evans, J. W.; Ellman, J. A. J. Org. Chem. 2003, 68, 9948-9957.
14. (i) Liu, G.; Cogan, D. A.; Owens, T. D.; Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 1278-1284.
15. (j) Kawecki, R. J. Org. Chem. 1999, 64, 8724-8727.
16. The triflates were synthesized according to a previously reported microwave method: Bengtson, A.; Hallberg, A.; Larhed, M. Org. Lett. 2002, 4, 1231-1233.
17. (a) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2-7.
18. (b) Larhed, M.; Hallberg, A. J. Org. Chem. 1997, 62, 7858-7862.
19. (c) Vallin, K. S. A.; Larhed, M.; Johansson, K.; Hallberg, A. J. Org. Chem. 2000, 65, 4537-4542.
20. Bengtson, A.; Larhed, M.; Hallberg, A. J. Org. Chem. 2002, 67, 5854-5856.
21. Alterman, M.; Björsne, M.; Muhlman, A.; Classon, B.; Kvarnström, I.; Danielson, H.; Markgren, P. O.; Nillroth, U.; Unge, T.; Hallberg, A.; Samuelsson, B. J. Med. Chem. 1998, 41, 3782-3792.
22. (a) Nillroth, U.; Vrang, L.; Markgren, P.-O.; Hulten, J.; Hallberg, A.; Danielson, U. H. Antimicrob. Agents Chemother. 1997, 41, 2383-2388.
23. (b) Danielson, U. H.; Lindgren, M. T.; Markgren, P.-O.; Nillroth, U. Adv. Exp. Med. Biol. 1998, 463, 99-103.