The first one-pot asymmetric synthesis of esters of highly biologically active (+)- and (-)- 3-[2-(6-methoxynaphthyl)]-2,2-dimethylpentanoic acid (Vallestril®)

Arkivoc

Volumn 2000, Issue 2 SPEC.ISS., 2000, Pages 95-102

  Hou, Yuqing ^a   Meyers, Cal Y ^a  

^a SOUTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; CHEMICAL COMPOUND; ESTER DERIVATIVE; FUNCTIONAL GROUP; METHALLENESTRIL;

ARTICLE; CHIRALITY; DIASTEREOISOMER; DRUG ACTIVITY; DRUG SYNTHESIS; MATERIALS; METHYLATION; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0008771676     PISSN: 14246376     EISSN: 14246376     Source Type: Journal    
DOI: None     Document Type: Article

References (27)

1. Courrier, R.; Horeau, A.; Jacques, J. Compt. Rend. Soc. Biol. 1947, 141, 159.
2. Horeau, A.; Jacques, J. Compt. Rend. 1947, 224, 862.
3. Courrier, R.; Horeau, A.; Jacques, J. Compt. Rend. 1947, 224, 1401.
4. Courrier, R.; Horeau, A.; Jacques, J. Compt. Rend. Soc. Biol. 1947, 141, 747.
5. Jacques, J.; Horeau, A. Bull Soc. Chim. Fr. 1948, 711.
6. Terenius, L. Acta Pharmacol. Toxicol. 1967, 25, 313.
7. Herbai, G. Acta Endocrinol. 1971, 68, 249.
8. Crawley, G. C. Hormones-Nonsteroidal Estrogens. In Kirk-Othmer Encyclopedia of Chemical Technology, 3rd Ed; Grayson, M., Eckroth, D., Eds.; Wiley: New York, 1980; 12, 670.
9. Sturnick, M. I.; Gargill, S. L. N. Engl. J. Med. 1952, 247, 830.
10. Schneeberg, N. G.; Perczek, L.; Nodine, J. H.; Perloff, W. H. J. Am. Med. Assoc. 1956, 161, 1062.
11. Soto, A. M.; Meyers, C. Y.; Sonnenschein, C. The Endocrine Society, 70th Annual Meeting, New Orleans, Abstract (1988).
12. Baker, V. L.; Draper, M.; Paul, S.; Allerheiligen, S.; Glant, M.; Shifren, J.; Jaffe, R. B. J. Clin. Endocrinol. Metab. 1998, 83, 6.
13. Banz, W. J.; Winters, T. A.; Hou, Y.; Adler, S.; Meyers, C. Y. Horm. Metab. Res. 1998, 30, 730.
14. Winters, T.; Banz, W.; Cameron, J.; McDearmon, M.; Debeljuk, L.; Huggenvik, J.; Collard, M.; Meyers, C.; Hou, Y.; Adler, S.; Dandliker W. Federation of American Societies for Experimental Biology, Experimental Biology Meeting, San Diego, April 15-18, 2000.
15. Meyers, C. Y.; Lutfi, H. G.; Adler, S. J. Steroid Biochem. Mol. Biol., 1997, 62, 477.
16. Jacques, J.; Horeau, A. French Patent 941289 (1949).
17. Wieland, P.; Miescher, K. Helv. Chim. Acta, 1948, 31, 1844.
18. Gay, R.; Horeau, A. Bull. Soc. Chim. France, 1955, 955.
19. Ciba Ltd, Swiss Patent 261123 (1949).
20. Ciba Ltd, British Patent 652003, (1951).
21. Jacques, J.; Horeau, A. Bull. Soc. Chim. France, 1949, 301.
22. Schmalz, H.-G. In Asymmetric Nucleophilic Addition to Electron Deficient Alkenes. Trost, B. M.; Fleming, I.; Heathcock, C. H.; Ley, S. V.; Noyori, R.; Paquette, L. A.; Pattenden, G.; Schreiber, S. L.; Semmelhack, M. F.; Winterfeldt, E. Eds.; Pergamon: Elmsford, NY, 1991.
23. Oppolzer, W.; Löher, H. J. Helv. Chim. Acta, 1981, 64, 2808.
24. See for example: (a) Oppolzer, W.; Tamura, O.; Deerberg, J. Helv. Chim. Acta, 1992, 75, 1965;
25. (b) Oppolzer, W.; Tamura, O.; Tetrahedron Lett. 1990, 31, 991;
26. Oppolzer, W.; Poli, G.; Kingma, A. J.; Starkemann, C.; Bernardinelli, G. Helv. Chim. Acta, 1987, 70, 2201.
27. Heer, J.; Billeter, J. R.; Miescher, K. Helv. Chim. Acta, 1945, 28, 1342.