A nonclassical stereoselective semi-synthesis of drospirenone via cross-metathesis reaction

Synthesis

Volumn , Issue 23, 2008, Pages 3801-3804

  Bandini, Marco ^a   Contento, Michele ^a   Garelli, Andrea ^a   Monari, Magda ^a   Tolomelli, Alessandra ^a   Umani Ronchi, Achille ^a   Andriolo, Erika ^b   Montorsi, Mauro ^b  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b NEWCHEM SpA   (Italy)

Author keywords

Cross metathesis; Drospirenone; Stereoselection; Steroids; Synthesis

Indexed keywords

CROSS-METATHESIS; DROSPIRENONE; STEREOSELECTION; STEROIDS; SYNTHESIS;

ESTERS;

3BETA,5 DIHYDROXY 6BETA,7BETA;15BETA,16BETA DIMETHYLENE 5BETA,17ALPHA PREGNANE 21,17 CARBOLACTONE; 6BETA,7BETA;15BETA,16BETA DIMETHYLENE 3 OXO 17ALPHA PREGN 4 ENE 21,17 CARBOLACTONE; 6BETA,7BETA;15BETA,16BETA DIMETHYLENE 5BETA,17 ALPHA PREGN 20 ENE 3BETA,5,17 TRIOL; DROSPIRENONE; ESTER; METHYL [3BETA,5,17BETA TRIHYDROXY 6BETA,7BETA;15BETA,16BETA DIMETHYLENE 5BETA ANDROSTAN 17ALPHA YL]PROPENOATE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG MECHANISM; DRUG STRUCTURE; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 57549115023     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1087226     Document Type: Article

References (20)

1. (a) Elger, W.; Beier, S.; Pollow, K.; Garfield, R.; Shi, S. Q.; Hillisch, A. Steroids 2003, 68, 891.
2. (b) Wiechert, R. In Analogue-based Drug Discovery; Fischer, J.; Ganellin, C. R., Eds.; Wiley-VCH: Berlin, 2006, Chap. 20, 395.
3. (c) Costantino, F.; Lenna, R.; Piuri, S. WO 2006,061,309, 2006.
4. (d) Seilz, C.; Seba, H. WO 2007,009,821, 2007.
5. Gálik, G.; Horváth, J.; Sörös, B.; Mahó, S.; Tuba, Z.; Balogh, G. WO 2006,059,168, 2006.
6. (a) Sam, K. M.; Auger, S.; Luu-The, V.; Poirier, D. J. Med. Chem. 1995, 38, 4518.
7. (b) Bittler, D.; Hofmeister, H.; Laurent, H.; Nickisch, K.; Nickolson, R.; Petzoldt, K.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1982, 21, 696;
8. Angew. Chem. 1982, 94, 718.
9. (c) Mohr, J.-Y.; Nickisch, K. US 6,933,395, 2005.
10. Waldemar, A.; Chantu, R. S.-M.; Pralhad, A. G. Chem. Rev. 2001, 101, 3499.
11. Crabtree, R. H. Science 2007, 318, 756.
12. (a) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003.
13. (b) Schrock, R. R.; Hoveyda, A. H. Angew. Chem. Int. Ed. 2003, 42, 4592.
14. (c) Connon, S. J.; Blechert, S. Angew. Chem. Int. Ed. 2003, 42, 1900.
15. (d) Astruc, D. New J. Chem. 2005, 29, 42.
16. (e) Clavier, H.; Grela, K.; Kirschning, A.; Mauduit, M.; Nolte, S. P. Angew. Chem. Int. Ed. 2007, 46, 6786.
17. (f) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem. Int. Ed. 2005, 44, 4490.
18. (g) Schrodi, Y.; Pedersen, R. L. Aldrichimica Acta 2007, 2, 45; and references therein.
19. Hoveyda, A. H.; Gillingham, D. G.; Van Veldhuizen, J. J.; Kataoka, O.; Garber, S. B.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biomol. Chem. 2004, 2, 8.
20. Nickisch, K.; Bittler, D.; Laurent, H.; Wiechert, R. Tetrahedron Lett. 1986, 27, 5463.