An unprecedented asymmetric Nazarov cyclization for the synthesis of nonracemic indanes as endothelin receptor antagonists

Synlett

Volumn , Issue 10, 1999, Pages 1612-1614

  Pridgen, Lendon N ^a   Huang, Kris ^a   Shilcrat, Susan ^a   Tickner Eldridge, Ann ^a   DeBrosse, Charles ^a   Haltiwanger, R Curtis ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

1,5 asymmetric induction; Asymmetric Nazarov cyclization; Endothelin receptor antagonists; Indanes

Indexed keywords

3 (2 CARBOXYMETHOXY 4 METHOXYPHENYL) 1 (3,4 METHYLENEDIOXYPHENYL) 5 PROPOXY 2 INDANCARBOXYLIC ACID; ENDOTHELIN RECEPTOR; ENDOTHELIN RECEPTOR ANTAGONIST; ENRASENTAN; INDAN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0032882713     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2912     Document Type: Article

References (19)

1. Elliot, J. D; Lago, M. A.; Cousins, R. D.; Gao, A.; Leber, J. D. Erhard, K. F.; Nambi, P.; Elshoursbagy, N. A.; Kumar, C.; Lee, J. A.; Bean, J. W.; DeBrosse, C. W.; Eggleston, D.S.; Brooks, D. P.; Feurerstein, G.; Ruffolo, R. R. Jr.; Weinstock, J.; Gleason, J.G.; Peishoff, C. E.; Ohlstein, E.H.; J. Med. Chem. 1994, 37, 1553.
2. Mills, R. J.; Ping, L.-J.; Kowalski, C. J. manuscript to be submitted.
3. Wood, J. L.; Mellinger, M.; Su, Q. manuscript to be submitted.
4. Clark, W. C.; Tickner-Eldridge, A. M.; Huang, G. K.; Pridgen, L. N.; Olsen, M. A.; Mills, R. J.; Lantos, I.; Baine, N. H. J. Am. Chem. Soc. 1998, 120, 4550. See also reference 6.
5. McGuire, M. A.; Shilcrat, S. C.; Sorenson, E. Tetrahedron Lett. 1999, 40, 3293.
6. Pridgen, L. N.; Huang, G. K. Tetrahedron Lett. 1998, 39, 8421.
7. A chiral auxiliary of opposite configuration may be substituted to obtain the enantiomer of 4a.
8. Habermas, K. L; Denmark, S. E. Jones, S. E. in Organic Reactions Vol. 45 Paquette, L. A. Ed.; John Wiley & Sons: New York, 1994, Vol. 45, p 1.
9. (a) Denmark, S. E. in Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: Oxford, 1991, Vol. 5, p 751.
10. (b) Ramaiah, M. Synthesis 1983, 429.
11. (c) Bender, J. A; Blize, A. E.; Browder, C. C.; Giese, S.; West, F. G J. Org. Chem. 1998, 63, 2430.
12. For relevant achiral examples of Nazarov cyclizations see; (a) Bergmann, J.; Venemalm, L. Tetrahedron Lett. 1987, 28, 3741.
13. (b) Sartori, G.; Bigi, F.; Maggi, R.; Luca, G.; Bernardi, G. L. Tetrahedron Lett. 1993, 34, 7339.
14. (c) Ichikawa, J.; Fujiwara, T.; Okauchi, T.; Minami, T. Synlett 1998, 927.
15. (d) Kajioka, T.; Oda, M.; Yamada, S.; Kawamori, Y.; Miyatake, R.; Kuroda, S. Synthesis 1999, 184.
16. (a) Tietze, L. F.; Schünke, C. Angew. Chem. Int. Ed., Engl. 1995, 34, 1731.
17. (b) Tietze, L. F.; Schünke, C. Eur. J. Org. Chem. 1998, 10, 2089.
18. 7: C, 69.73; H, 5.04; N 2.80. Found: C, 70.00; H, 4.75; N, 2.83.
19. 2 using SHELXL-93 (G. M. Sheldrick, Gottingen, 1993). All non-hydrogen atoms were refined anisotropically and hydrogen atoms were included in idealized positions with a riding model. Final R values are R1 = 0.046 (I > 2σ (I)) and wR2 - 0.134 (all data). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-102250. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: int. code + (44)1223 336-033; e-mail: deposit@ccdc.cam.ac.uk).