An efficient enantioselective synthesis of the D1 agonist (5aR,11bS)-4,5,5a,6,7,11b-hexahydro-2-propyl-3-thia-5-azacyclopenta[c] phenanthrene-9,10-diol (A-86929)

Journal of Organic Chemistry

Volumn 62, Issue 9, 1997, Pages 2782-2785

  Ehrlich, Paul P ^a   Ralston, Jeffrey W ^a   Michaelides, Michael R ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4,5,5A,6,7,11B HEXAHYDRO 9,10 DIHYDROXY 2 PROPYL 3 THIA 5 AZACYCLOPENT 1 ENA[C]PHENANTHRENE; DOPAMINE 1 RECEPTOR STIMULATING AGENT; PHENANTHRENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER;

EID: 0030974395     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970066l     Document Type: Article

References (8)

1. Shiosaki, K.; Jenner, P.; Asin, K. E.; Britton, D.; Lin, C. W.; Michaelides, M. R.; Smith, L.; Bianchi, B.; DiDomenico, S., Jr.; Hodges, L.; Hong, Y.; Mahan, L.; Mikusa, J.; Miller, T.; Nikkel, A.; Stashko, M.; Witte, D.; Williams, M. J. Pharmacol. Exp. Ther. 1996, 276, 150-160.
2. Michaelides, M. R.; Hong, Y.; DiDomenico, S., Jr; Asin, K. E.; Britton, D. R.; Lin, C. W.; Williams, M.; Shiosaki, K. J. Med. Chem. 1995, 38, 3445-3447.
3. Lapidus, M.; Sweeney, M. J. J. Med Chem. 1973, 16, 163.
4. Norlander, E. J.; Payne, M. J.; Njoroge, F. G.; Vishwanath, V. M.; Han, G. B.; Laikos, G. D., Balk, M. A. J. Qrg. Chem. 1985, 50, 3619-3622.
5. Angelastro, M. R.; Peet, Norton, P. P.; Bey, P. J. Org. Chem. 1989, 54, 3913-3916.
6. Enantiomeric excess was determined utilizing an analytical Chiracel OD column purchased from Chiral Technologies Inc., 730 Springdale Dr., Exton, PA. The mobile phase was 9:1 hexanes:iPA, detection = 254 nm, flow = 1mL/min.
7. Purchased from Aldrich Chemical Company, Inc., Milwaukee, WI 53233.
8. Alvarez-Insua, A. S.; Conde, S.; Corral, C. J. Heterocycl. Chem. 1982, 19, 713-716.