An effective route to (-)-aphanorphine using D-tyrosine as a chiral building block

Synthesis

Volumn , Issue 1, 2007, Pages 55-60

  Li, Min ^a   Zhou, Peijie ^a   Roth, Hans F ^b  

^a GEORGETOWN UNIVERSITY MEDICAL CENTER   (United States)

^b Orgchem Technologies Inc   (United States)

Author keywords

Aphanorphine; C H insertion; Intra annular chirality transfer; Rhodium 1,3 dicarbonyl carbenoid; Thioketal

Indexed keywords

APHANORPHINE; C-H INSERTION; INTRA-ANNULAR CHIRALITY TRANSFER; RHODIUM 1,3-DICARBONYL CARBENOID; THIOKETAL;

CHEMICAL BONDS; CHIRALITY; REACTION KINETICS; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

AMINO ACIDS;

APHANORPHINE; TERT BUTYLOXYCARBONYL DEXTRO TYROSINE; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; STEREOCHEMISTRY;

EID: 33947512904     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-958931     Document Type: Article

References (39)

1. For a review of the synthesis of pentazocine(2) and related benzomorphans, see: Palmer, D. C; Strauss, M. J. Chem. Rev. 1977, 77, 1.
2. Gulavita, N.; Hori, A.; Shimizu, Y.; Laszlo, P.; Clardy, J. Tetrahedron Lett. 1988, 29, 4381.
3. For a detailed literature on the synthesis of 1, see: Bower, J. F.; Szeto, P.; Gallagher, T. Chem. Commun. 2005, 5793; and references cited therein.
4. (a) Fadel, A.; Arzel, P. Tetrahedron: Asymmetry 1997, 8, 371.
5. (b) Fadel, A.; Arzel, P. Tetrahedron: Asymmetry 1995, 6, 893.
6. (a) Tamura, O.; Yanagimachi, T.; Ishibashi, H. Tetrahedron: Asymmetry 2003, 14, 3033.
7. (b) Tamura, O.; Yanagimachi, T.; Kobayashi, T.; Ishibashi, H. Org. Lett. 2001, 3, 2427.
8. Fuchs, J. R.; Funk, R. L. Org. Lett. 2001, 3, 3923.
9. (a) Zhai, H.; Luo, S.; Ye, C.; Ma, Y. J. Org. Chem. 2003, 68, 8268.
10. (b) Hu, H.; Zhai, H. Synlett 2003, 2129.
11. Katoh, M.; Inoue, H.; Suzuki, A.; Honda, T. Synlett 2005, 2820.
12. Bower, J. F.; Svenda, J.; Williams, A. J.; Charmant, J. P. H.; Lawrence, R. M.; Szeto, P.; Gallagher, T. Org. Lett. 2004, 6, 4727; and references cited therein.
13. For examples of Weinreb amide formation, see: (a) Ruiz, J.; Sotomayor, N.; Lete, E. Org. Lett. 2003, 5, 1115.
14. (b) Davis, F. A.; Prasad, K. R.; Nolt, M. B.; Wu, Y. Org. Lett. 2003, 5, 925.
15. (c) Conrad, R. M.; Grogan, M. J.; Bertozzi, C. R. Org. Lett. 2002, 4, 1359.
16. (a) Bouazza, F.; Renoux, B.; Bachmann, C.; Gesson, J.-P. Org. Lett. 2003, 5, 4049.
17. (b) Johnson, C. R.; Senanayake, C. H. J. Org. Chem. 1989, 54, 736.
18. Chiralcel OD-H column (100 x 4.6 mm), hexanes-i-PrOH (10: 90), 1.0 mL/min, 23°C, λ = 276 nm, retention time 6.9 min (D- 7) and 7.7 min (L-7).
19. (a) Sasaki, S.; Hamada, Y.; Shioiri, T. Synlett 1999, 453.
20. (b) Walkup, R. D.; Boatman, P. D.; Kane, R. R.; Cunningham, R. T. Tetrahedron Lett. 1991, 32, 3937.
21. Regitz, M.; Rüter, J.; Liedhegener, A. Org. Synth. Coll. Vol. VI; Wiley: New York, 1988, 388; and references cited therein.
22. (a) Jiang, N.; Li, C.-J. Chem. Commun. 2004, 394.
23. (b) Zhu, S.-Z.; He, P. Curr. Org. Chem. 2004, 8, 97.
24. For a review, see: (c) Marchard, A. P.; Macbrockway, N. Chem. Rev. 1974, 74, 431.
25. (a) von E. Doering, W.; Knox, L. H. J. Am. Chem. Soc. 1957, 79, 352.
26. (b) Buchner, E.; Schottenhammer, K. Ber. Dtsch. Chem. Ges. 1920, 53, 865.
27. Moody, C. J.; Doyle, K. J.; Elliot, M. C.; Mowlew, T. J. Pure. Appl. Chem. 1994, 66, 2107; and references cited therein.
28. Denmark, S. E.; Nakajima, N.; Nicaise, O. J. J. Am. Chem. Soc. 1994, 116, 8797.
29. For reviews, see: (a) Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013.
30. (b) Nelson, A. Angew. Chem. Int. Ed. 1999, 38, 1583.
31. (a) Murakami, N.; Tamura, S.; Wang, W.; Takagi, T.; Kobayashi, M. Tetrahedron 2001, 57, 4323.
32. (b) Spivey, A. C.; Srikaran, R. Annu. Rep. Prog. Chem., Sect. B 2001, 97, 41.
33. (c) Gao, C; Lin, C.-H.; Lo, C.-H.; Mao, S.; Wirsching, P.; Lerner, R. A.; Janda, K. D. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 11777.
34. Li, P.; Xu, J.-C. J. Pept. Res. 2001, 58, 129.
35. (a) Muthusamy, S.; Babu, S. A.; Guanathan, C. Tetrahedron Lett. 2001, 42, 359.
36. (b) Kaufman, T. S.; Gonzalez-Sierra, M.; Ruveda, E. A. J. Chem. Soc, Perkin Trans. 1 1988, 2323.
37. (a) Ong, B. S.; Chan, T. H. Synth. Commun. 1977, 7, 283.
38. (b) Evans, D. A.; Grimm, K. G.; Truesdale, L. K. J. Am. Chem. Soc. 1975, 97, 3229.
39. Shiotani, S.; Okada, H.; Nakamata, K.; Yamamoto, T.; Sekino, F. Heterocycles 1996, 43, 1031.