Asymmetric synthesis of (+)-L-733, 060 and (+)-CP-99, 994 based on a new chiral 3-piperidinol synthon

Organic Letters

Volumn 5, Issue 11, 2003, Pages 1927-1929

  Huang, Pei Oiang ^a   Liu, Liang Xian ^a   Wei, Bang Guo ^a   Ruan, Yuan Ping ^a  

^a XIAMEN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

3 (2 METHOXYBENZYLAMINO) 2 PHENYLPIPERIDINE; 3 [3,5 BIS(TRIFLUOROMETHYL)BENZYLOXY] 2 PHENYLPIPERIDINE; ANTIEMETIC AGENT; GLUTAMIC ACID; GLUTARIMIDE; LEWIS ACID; OXIME; PIPERIDINE DERIVATIVE; SUBSTANCE P ANTAGONIST; 3-(2-METHOXYBENZYLAMINO)-2-PHENYLPIPERIDINE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; NEUROKININ 1 RECEPTOR;

ACETYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; DRUG SYNTHESIS; REDUCTION; STEREOCHEMISTRY; CHEMISTRY; DRUG ANTAGONISM; MEDICINAL PLANT; STEREOISOMERISM; SYNTHESIS;

ACETYLATION; GLUTAMIC ACID; INDICATORS AND REAGENTS; PIPERIDINES; PLANTS, MEDICINAL; RECEPTORS, NEUROKININ-1; STEREOISOMERISM;

EID: 0042630562     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034505g     Document Type: Article

References (28)

1. (a) Baker, R.; Harrison, T.; Hollingworth, G. J.; Swain, C. J.; Williams, B. J. EP 0 528, 495A1, 1993.
2. (b) Harrison, T.; Williams, B. J.; Swain, C. J.; Ball, R. G. Bioorg. Med. Chem. Lett. 1994, 4, 2545.
3. Desai, M. C.; Lefkowitz, S. L.; Thadeio, P. F.; Longo, K. P.; Snider, R. M. J. Med. Chem. 1992, 35, 4911.
4. (a) Lotz, M.; Vaughan, J. H.; Carson, D. A. Science 1988, 241, 1218.
5. (b) Perianan, A.; Snyderman, R.; Malfroy, B. Biochem. Biophys. Res. Commun. 1989, 161, 520.
6. (c) Moskowitz, M. A. Trends Pharmacol. Sci. 1992, 13, 307.
7. (d) Zaman, S.; Woods, A. J.; Watson, J. W.; Reynolds, D. J. M.; Andrews, P. L. R. Neuropharmacology 2000, 39, 316.
8. (a) Calvez, O.; Langlois, N. Tetrahedron Lett. 1999, 40, 7099.
9. (b) Stadler, H.; Bos, M. Heterocycles 1999, 51, 1067.
10. (c) Tomooka, K.; Nakazaki, A.; Nakai, T. J. Am. Chem. Soc. 2000, 122, 408.
11. (d) Lee, J.; Hoang, T.; Lewis, S.; Weissman, S. A.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 2001, 42, 6223.
12. (e) Bhaskar, G.; Rao, B. V. Tetrahedron Lett. 2003, 44, 915.
13. (a) Chandrasekhar, S.; Mohanty, P. K. Tetrahedron Lett. 1999, 40, 5071.
14. (b) Tsuritani, N.; Yamada, K.; Yoshikawa, N.; Shibasaki, M. Chem. Lett. 2002, 276.
15. (c) Yamazaki, N.; Atobe, M.; Kibayashi, C. Tetrahedron Lett. 2002, 43, 7979.
16. For the synthesis of racemic CP-99, 994, see: (d) Desai, M. C.; Thadeio, P. F.; Lefkowitz, S. L. Tetrahedron Lett. 1993, 34, 5831.
17. (a) Huang, P.-Q.; Wang, S. L.; Zheng, H.; Fei, X. S. Tetrahedron Lett. 1997, 38, 271.
18. (b) Huang, P.-Q.; Wang, S. L.; Ye, J. L.; Ruan, Y. P.; Huang, Y. Q.; Zheng, H.; Gao, J. X. Tetrahedron 1998, 54, 12547.
19. (c) Huang, P.-Q.; Wang, S. L.; Ruan, Y. P.; Gao, J. X. Nat. Prod. Lett. 1998, 11, 101.
20. (d) Huang, P.-Q.; Ye, J. L.; Chen, Z.; Ruan, Y. P.; Gao, J. X. Synth. Commun. 1998, 28, 417.
21. (e) Huang, P. -Q.; Chen, Q. F.; Chen, C.-L.; Zhang, H.-K. Tetrahedron: Asymmetry 1999, 10, 3827.
22. (f) Huang, P.-Q.; Zheng, X.; Wang, S. L.; Ye, J. L.; Jin, L. R.; Chen, Z. Tetrahedron: Asymmetry 1999, 10, 3309.
23. (g) Zheng, X.; Huang, P.-Q.; Ruan, Y. P.; Lee, A. W. M.; Chan, W. H. Heterocycles 2001, 55, 1505.
24. (h) Zheng, X.; Huang, P.-Q.; Ruan, Y. P.; Lee, A. W. M.; Chan, W. H. Nat. Prod. Lett. 2002, 16, 53.
25. (i) Huang, P.-Q.; Zheng, X. Arkivoc 2003, Part ii, 7 (http://www.arkatusa.org).
26. Gringore, O. H.; Rouessac, F. P. In Organic Synthesis; Freeman, J. P. Ed.; John Wiley & Sons: New York, 1990; Coll. Vol. VII, p 99.
27. For a recent review, see: Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817.
28. Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651.