Stereoselective synthesis of new digitalis-like perhydroindene derivatives from the Hajos-Parrish ketone

Synlett

Volumn , Issue 11, 1998, Pages 1234-1236

  Almirante, Nicoletta ^a   Cerri, Alberto ^a   De Munari, Sergio ^a  

^a Prassis Sigma Tau Research Institute   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001898541     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1902     Document Type: Article

References (21)

1. Hoffmann, B. F.; Bigger, J. T. Jr. In The Pharmacological Basis of Therapeutics; Goodman Gilman, A.; Rall, T. W.; Nies, A. S.; Taylor, P., Eds; Pergamon Press Inc., 1990; p. 814.
2. Hajos, Z. G; Parrish, D. R. J. Org. Chem. 1974, 39, 1615.
3. Medarde, M.; Tomé, F.; López, J.L.; Caballero, E.; Boya, M.; Melero, C.P.; San Feliciano, A. Tetrahedron Lett. 1994, 35, 8683.
4. Frigerio, M.; Santagostino, M.; Sputore, S. Synlett 1997, 833.
5. While we were submitting this manuscript, two papers, reporting a synthetic approach to complex cardenolides starting from the 3a,4-anhydro derivative of 1, appeared in the literature: a) Overman, L.E.; Rucker, P.V. Tetrahedron Lett. 1998, 39, 4643;
6. b) Hynes, J.H. Jr; Overman, L.E.; Nasser, T.; Rucker, P.V. Tetrahedron Lett. 1998, 39, 4647
7. a) Daniewski, A. R.; Kabat, M. M.; Masnyk, M.; Wicha, J.; Wojciechowska, W.; Duddeck, H, J. Org. Chem. 1988, 53, 4855.
8. b) Daniewski, A. R.; Kabat, M. M.; Masnyk, M.; Wojciechowska, W; Wicha, J., Collect. Czech. Chem. Commun. 1991, 56, 1064.
9. Almirante, N.; Cerri, A. J. Org. Chem. 1997, 62, 3402.
10. For a higher-yielding conversion of the 17β-CN group into the butenolide moiety see Stork, G; West, F.; Lee, H. Y; Isaacs, R. C. A.; Manabe, S., J. Am. Chem. Soc. 1996, 118, 10660.
11. Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904.
12. 4 in EtOAc with almost complete inversion of configuration (β/α 85:15, 80% yield).
13. Compounds 4a,b were obtained by treatment of the crude hydrazones of 3a,b with iodine and, successively, reduction of the 1-iodo-1,2-didehydro derivatives with diimide, as described for the 5β,14β-androst-9(11)-ene nucleus, by Daniewski (ref 6a).
14. 7 it allowed the complete conversion of the intermediate anhydride 5a,b to compounds 6a,b (each one isolated as an almost 60:40 diastereoisomeric mixture) and prevented the dehydration of the acid labile 3aβ-hydroxy function.
15. Soai, K.; Oyamada, H. Synthesis 1984, 605.
16. For the critical workup of this reaction see ref 7. Compounds 7a,b were isolated, each one, as an almost 55:45 diastereoisomeric mixture.
17. Mukai, C.; Moharram, S. M.; Azukizawa, S.; Hanaoka, M., J. Org. Chem., 1997, 62, 8095.
18. Wilson, L. J.; Liotta, D. C. J. Org. Chem. 1992, 57, 1948.
19. 3: C, 75.43; H, 9.50. Found: C, 75.37; H, 9.58.
20. Brown, L.; Erdmann, E. Arzneim.-Forsch. 1984, 34, 1314.
21. Doucet, A.; Hus-Citharel, A.; Morel, F. Am. J. Physiol. 1986, 251, F851.