Asymmetric synthesis of a dopamine D1 agonist, dihydrexidine from d-serine

Tetrahedron Asymmetry

Volumn 22, Issue 14-15, 2011, Pages 1522-1529

  Malhotra, Rajesh ^a   Ghosh, Amit ^a,b   Ghosh, Rajib ^a,b   Chakrabarti, Sagar ^a,b   Dutta, Swarup ^b   Dey, Tushar K ^a,b   Roy, Subho ^b   Basu, Sourav ^b   Hajra, Saumen ^c  

^a GURU JAMBHESHWAR UNIVERSITY OF SCIENCE AND TECHNOLOGY   (India)

^b Molecular Modeling Section   (India)

^c INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 6,7 DIMETHOXY 1 PHENYLTETRALIN; DEXTRO SERINE; DIHYDREXIDINE; DOPAMINE 1 RECEPTOR STIMULATING AGENT; N NOSYL 2 AMINO 1 PHENYLTETRALIN; TETRALIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; FRIEDEL CRAFTS REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; WITTIG REACTION;

EID: 80054922984     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2011.08.014     Document Type: Article

References (23)

1. W.K. Brewster, D.E. Nichols, R.M. Riggs, D.M. Mottola, T.W. Lovenberg, M.H. Lewis, and R.B. Mailman J. Med. Chem. 33 1990 1756 1764
2. J.R. Taylor, M.S. Lawrence, D.E. Redmont, J.D. Elsworth, R.H. Roth, D.E. Nochols, and R.B. Mailman Eur. J. Pharmacol. 199 1991 389 391
3. M.P. Seiler, A. Hagenbach, H.-J. Wüthrich, and R. Marksteun J. Med. Chem. 34 1991 303 307
4. T.A. Knoerzer, D.E. Nichols, W.K. Brewster, V.J. Watts, D. Mottola, and R.B. Mailman J. Med. Chem. 37 1994 2453 2460
5. M.R. Michaelides, Y. Hong Jr., S. DiDomenico, K.E. Asin, D.R. Britton, C.W. Lin, M. Williams, and K. Shiosaki J. Med. Chem. 38 1995 3445 3447
6. X. Huang, C.P. Lawler, M.M. Lewis, D.E. Nichols, and R.B. Mailman Int. Rev. Neurobiol. 48 2001 65 139
7. M.S. George, C.E. Molnar, E.L. Grenesko, B. Anderson, Q. Mu, K. Johnson, Z. Nahas, M. Knable, P. Fernandes, J. Juncos, X. Huang, D.E. Nichols, and R.B. Mailman Schizophr. Res. 93 2007 42 50
8. P.S. Goldman-Rakic, S.A. Castner, T.H. Svensson, L.J. Siever, and G.V. Williams Psychopharmacology (Berl.) 2004 3 16
9. Q. Mu, K. Johnson, P.S. Morgan, E.L. Grenesko, C.E. Molnar, B. Anderson, Z. Nahas, F.A. Kozel, S. Kose, M. Knable, P. Fernandes, D.E. Nichols, R.B. Mailman, and M.S. George Schizophr. Res. 94 2007 332 341
10. D.E. Nichols, and M.M. Lewis Med. Chem. Res. 13 2004 105 126
11. J. Zhang, B. Xiong, X. Zhen, and A. Zhang Med. Res. Rev. 29 2009 272 294
12. K. Negash, and D.E. Nichols Tetrahedron Lett. 37 1996 6971 6972
13. J.P. Cueva, and D.E. Nichols Synthesis 2009 715 720
14. Ehrlich, P. P.; Michaelides, M. R.; McLaughlin, M. M.; Hsaio, C. US 5659037, 1997.
15. Y. Asano, M. Yamashita, K. Nagai, M. Kuriyama, K.I. Yamada, and K. Tomioka Tetrahedron Lett. 42 2001 8493 8495
16. M. Yamashita, K.I. Yamada, and K. Tomioka Tetrahedron 60 2004 4237 4242
17. S. Hajra, and S. Bar Tetrahedron: Asymmetry 22 2011 775 779
18. S. Hajra, and S. Bar Chem. Commun. 47 2011 3981 3982
19. P. Garner, and J.M. Park J. Org. Chem. 52 1987 2361 2364
20. L. Williams, Z. Zhang, F. Shao, P.J. Carroll, and M.M. Joullie Tetrahedron 52 1996 11673 11694
21. A. Mengel, and O. Reiser Chem. Rev. 99 1999 1191 1223
22. A. Husain, and B. Ganem Tetrahedron Lett. 43 2002 8621 8623
23. The specific rotation of dihydrexidine as hydrobromide salt 1·HBr has not been previously reported.