New approaches to the industrial synthesis of HIV protease inhibitors

Organic and Biomolecular Chemistry

Volumn 2, Issue 14, 2004, Pages 2061-2070

  Honda, Yutaka ^a   Katayama, Satoshi ^a   Kojima, Mitsuhiko ^a   Suzuki, Takayuki ^a   Kishibata, Naomi ^a   Izawa, Kunisuke ^a  

^a AJINOMOTO CO INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTALLIZATION; DISTILLATION; ESTERS; ETHANOL; HALOGENATION; HYDROGENATION; ORGANIC ACIDS; ORGANIC SOLVENTS; SYNTHESIS (CHEMICAL);

AMINO EPOXIDE; HALOMETHYL KETONES; HIV PROTEASE INHIBITORS; MALIC ACID;

AMINO ACIDS;

HUMAN IMMUNODEFICIENCY VIRUS;

AMPRENAVIR; AMPRENAVIR PHOSPHATE; CARBAMIC ACID DERIVATIVE; FURAN DERIVATIVE; ORGANOPHOSPHATE; PROTEINASE INHIBITOR; SULFONAMIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; SYNTHESIS;

CARBAMATES; FURANS; HIV PROTEASE INHIBITORS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PHOSPHORIC ACID ESTERS; SULFONAMIDES;

EID: 3843132927     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b404071f     Document Type: Review

References (54)

1. For progress in the treatment of HIV with HAART, for example, see: (a) T. W. Chun, D. Engel, S. B. Mizell, C. W. Halkhan, M. Fischette, S. Park, R. T. Davey, M. Dybul, J. A. Kovacs, J. A. Metcalf, J. M. Mican, M. Berrey, L. Corey, H. C. Lane and A. S. Fauci, Nat. Med., 1999, 5, 651-655; (b) S. Glushakova, L. Dubrovsky, J.-C. Grivel, O. Haffar and M. Bukrinsky, Antiviral Res., 2000, 47, 89-95.
2. For progress in the treatment of HIV with HAART, for example, see: (a) T. W. Chun, D. Engel, S. B. Mizell, C. W. Halkhan, M. Fischette, S. Park, R. T. Davey, M. Dybul, J. A. Kovacs, J. A. Metcalf, J. M. Mican, M. Berrey, L. Corey, H. C. Lane and A. S. Fauci, Nat. Med., 1999, 5, 651-655; (b) S. Glushakova, L. Dubrovsky, J.-C. Grivel, O. Haffar and M. Bukrinsky, Antiviral Res., 2000, 47, 89-95.
3. (a) R. D. Tung, M. A. Murcko and G. R. Bhisetti, Vertex Pharmaceutical Inc., PCT Int. Appl., WO9405639, 1994;
4. (b) E. E. Kim, C. T. Baker, M. D. Dwyer, M. A. Murcko, B. G. Rao, R. D. Tung and M. A. Navia, J. Am. Chem. Soc., 1995, 117, 1181-1182.
5. (a) R. D. Tung, M. R. Hale, C. T. Baker, E. S. Furfine, I. Kaldor, W. W. Kazmierski and A. R. Spaltenstein, Vertex Pharmaceuticals, PCT Int. Appl., WO9933815, 1999;
6. (b) R. D. Tung, M. R. Hale, C. T. Baker, E. S. Furfine, I. Kaldor, W. W. Kazmierski and A. R. Spaltenstein, Vertex Pharmaceuticals, U.S. Patent 6 559 137, 2003.
7. E. Al-Farhan, D. D. Deininger, S. S. McGhie, J. O'Callaghan, M. S. Robertson, K. Rodgers, S. J. Rout, H. Singh and R. D. Tung, Glaxo Group Ltd., PCT Int. Appl., WO9948885, 1999.
8. (a) N. Shibata, T. Katoh and S. Terashima, Tetrahedron Lett., 1997, 38, 619-620;
9. (b) E. J. Corey and F.-Y. Zhang, Angew. Chem., Int. Ed. Engl., 1999, 38, 1931-1934;
10. (c) B. M. Kim, S. J. Bae, S. M. So, H. Y. Yoo, S. K. Chang, J. H. Lee and J. Kang, Org. Lett., 2001, 3, 2349-2351;
11. (d) A. K. Ghosh, J. F. Kincaid, W. Cho, D. E. Walters, K. Krishnan, K. A. Hussain, Y. Koo, H. Cho, C. Rudall, L. Holland and J. Buthod, Bioorg. Med. Chem. Lett., 1998, 8, 687-690.
12. (a) T. Kamijo, T. Yamaguchi, T. Yanagi, I. Tsuchiya and H. Takeuchi, Kissei Pharmaceutical Co., Ltd., Japan Kokai Tokkyo Koho, JP09071584, 1997;
13. (b) T. Kamijo, T. Yamaguchi, T. Yanagi, I. Tsuchiya and H. Takeuchi, Kissei Pharmaceutical Co., Ltd., Japan Kokai Tokkyo Koho, JP09124630, 1997.
14. For the preparation of N-protected amino epoxide and conversion to HIV protease inhibitors, see: (a) P. L. Beaulieu, D. Wernic, J.-S. Duceppe and Y. Guindon, Tetrahedron Lett., 1995, 36, 3317-3320; (b) J. S. Ng, C. A. Przybyla, C. Liu, C. Yen, F. W. Muellner and C. L. Weyker, Tetrahedron, 1995, 51, 6397-6410; (c) C. Liu, J . S. Ng, J. R. Behling, C. H. Yen, A. L. Campbell, K. S. Fuzail, F. E. Yonan and D. V. Mehrota, Org. Proc. Res. Dev., 1997, 1, 45-54.
15. For the preparation of N-protected amino epoxide and conversion to HIV protease inhibitors, see: (a) P. L. Beaulieu, D. Wernic, J.-S. Duceppe and Y. Guindon, Tetrahedron Lett., 1995, 36, 3317-3320; (b) J. S. Ng, C. A. Przybyla, C. Liu, C. Yen, F. W. Muellner and C. L. Weyker, Tetrahedron, 1995, 51, 6397-6410; (c) C. Liu, J . S. Ng, J. R. Behling, C. H. Yen, A. L. Campbell, K. S. Fuzail, F. E. Yonan and D. V. Mehrota, Org. Proc. Res. Dev., 1997, 1, 45-54.
16. For the preparation of N-protected amino epoxide and conversion to HIV protease inhibitors, see: (a) P. L. Beaulieu, D. Wernic, J.-S. Duceppe and Y. Guindon, Tetrahedron Lett., 1995, 36, 3317-3320; (b) J. S. Ng, C. A. Przybyla, C. Liu, C. Yen, F. W. Muellner and C. L. Weyker, Tetrahedron, 1995, 51, 6397-6410; (c) C. Liu, J . S. Ng, J. R. Behling, C. H. Yen, A. L. Campbell, K. S. Fuzail, F. E. Yonan and D. V. Mehrota, Org. Proc. Res. Dev., 1997, 1, 45-54.
17. For the preparation of amino epoxide 9b from chlorohydrin 7b, see: P. L. Beaulieu and D. Wernic, J. Org. Chem., 1996, 61, 3635-3645.
18. For synthetic approaches to halomethyl ketones, see: (a) D. P. Getman, G. A. DeCrescenzo, R. M. Heintz, K. L. Reed, J. J. Talley, M. L. Bryant, M. Clare, K. A. Houseman, J. Marr, R. A. Mueller, M. L. Vazques, H.-S. Shieh, W. C. Stallings and R. A. Stegeman, J. Med. Chem., 1993, 36, 288-291; (b) P. Raddatz, A. Jonczyk, K.-O. Minck, C. J. Schmitges and J. Sombroek, J. Med. Chem., 1991, 34, 3267-3280; (c) L. E. Fisher and J. M. Muchowski, Org. Prep. Proc. Int., 1990, 22, 399-484; (d) A. Heinsoo, G. Raidaru, K. Linask, J. Jarv, M. Zetterstrom and U. Langel, Tetrahedron: Asymmetry, 1995, 6, 2245-2247; (e) B. K. Handa, P. J. Machin, J. A. Martin, S. Redshaw and G. J. Thomas, F. Hoffmann La Roche AG, Eur. Pat. Appl., EP346847, 1989; (f) A. Albeck and R. Persky, Tetrahedron, 1994, 50, 6333-6346; (g) A. Nishiyama, T. Sugawa, H. Manabe, K. Inoue and N. Yoshida, Kaneka Corp., U.S. Patent 5 929 284, 1999; (h) P. Chen, P. T. W. Cheng, S. H. Spergel, R. Zahler, X. Wang, J. Thottathil, J. C. Barrish and R. P. Polniaszek, Tetrahedron Lett., 1997, 38, 3175-3187; (i) J. Barluenga, B. Baragana, A. Alonso and J. M. Concellon, J. Chem. Soc., Chem. Commun., 1994, 969-970.
19. For synthetic approaches to halomethyl ketones, see: (a) D. P. Getman, G. A. DeCrescenzo, R. M. Heintz, K. L. Reed, J. J. Talley, M. L. Bryant, M. Clare, K. A. Houseman, J. Marr, R. A. Mueller, M. L. Vazques, H.-S. Shieh, W. C. Stallings and R. A. Stegeman, J. Med. Chem., 1993, 36, 288-291; (b) P. Raddatz, A. Jonczyk, K.-O. Minck, C. J. Schmitges and J. Sombroek, J. Med. Chem., 1991, 34, 3267-3280; (c) L. E. Fisher and J. M. Muchowski, Org. Prep. Proc. Int., 1990, 22, 399-484; (d) A. Heinsoo, G. Raidaru, K. Linask, J. Jarv, M. Zetterstrom and U. Langel, Tetrahedron: Asymmetry, 1995, 6, 2245-2247; (e) B. K. Handa, P. J. Machin, J. A. Martin, S. Redshaw and G. J. Thomas, F. Hoffmann La Roche AG, Eur. Pat. Appl., EP346847, 1989; (f) A. Albeck and R. Persky, Tetrahedron, 1994, 50, 6333-6346; (g) A. Nishiyama, T. Sugawa, H. Manabe, K. Inoue and N. Yoshida, Kaneka Corp., U.S. Patent 5 929 284, 1999; (h) P. Chen, P. T. W. Cheng, S. H. Spergel, R. Zahler, X. Wang, J. Thottathil, J. C. Barrish and R. P. Polniaszek, Tetrahedron Lett., 1997, 38, 3175-3187; (i) J. Barluenga, B. Baragana, A. Alonso and J. M. Concellon, J. Chem. Soc., Chem. Commun., 1994, 969-970.
20. For synthetic approaches to halomethyl ketones, see: (a) D. P. Getman, G. A. DeCrescenzo, R. M. Heintz, K. L. Reed, J. J. Talley, M. L. Bryant, M. Clare, K. A. Houseman, J. Marr, R. A. Mueller, M. L. Vazques, H.-S. Shieh, W. C. Stallings and R. A. Stegeman, J. Med. Chem., 1993, 36, 288-291; (b) P. Raddatz, A. Jonczyk, K.-O. Minck, C. J. Schmitges and J. Sombroek, J. Med. Chem., 1991, 34, 3267-3280; (c) L. E. Fisher and J. M. Muchowski, Org. Prep. Proc. Int., 1990, 22, 399-484; (d) A. Heinsoo, G. Raidaru, K. Linask, J. Jarv, M. Zetterstrom and U. Langel, Tetrahedron: Asymmetry, 1995, 6, 2245-2247; (e) B. K. Handa, P. J. Machin, J. A. Martin, S. Redshaw and G. J. Thomas, F. Hoffmann La Roche AG, Eur. Pat. Appl., EP346847, 1989; (f) A. Albeck and R. Persky, Tetrahedron, 1994, 50, 6333-6346; (g) A. Nishiyama, T. Sugawa, H. Manabe, K. Inoue and N. Yoshida, Kaneka Corp., U.S. Patent 5 929 284, 1999; (h) P. Chen, P. T. W. Cheng, S. H. Spergel, R. Zahler, X. Wang, J. Thottathil, J. C. Barrish and R. P. Polniaszek, Tetrahedron Lett., 1997, 38, 3175-3187; (i) J. Barluenga, B. Baragana, A. Alonso and J. M. Concellon, J. Chem. Soc., Chem. Commun., 1994, 969-970.
21. For synthetic approaches to halomethyl ketones, see: (a) D. P. Getman, G. A. DeCrescenzo, R. M. Heintz, K. L. Reed, J. J. Talley, M. L. Bryant, M. Clare, K. A. Houseman, J. Marr, R. A. Mueller, M. L. Vazques, H.-S. Shieh, W. C. Stallings and R. A. Stegeman, J. Med. Chem., 1993, 36, 288-291; (b) P. Raddatz, A. Jonczyk, K.-O. Minck, C. J. Schmitges and J. Sombroek, J. Med. Chem., 1991, 34, 3267-3280; (c) L. E. Fisher and J. M. Muchowski, Org. Prep. Proc. Int., 1990, 22, 399-484; (d) A. Heinsoo, G. Raidaru, K. Linask, J. Jarv, M. Zetterstrom and U. Langel, Tetrahedron: Asymmetry, 1995, 6, 2245-2247; (e) B. K. Handa, P. J. Machin, J. A. Martin, S. Redshaw and G. J. Thomas, F. Hoffmann La Roche AG, Eur. Pat. Appl., EP346847, 1989; (f) A. Albeck and R. Persky, Tetrahedron, 1994, 50, 6333-6346; (g) A. Nishiyama, T. Sugawa, H. Manabe, K. Inoue and N. Yoshida, Kaneka Corp., U.S. Patent 5 929 284, 1999; (h) P. Chen, P. T. W. Cheng, S. H. Spergel, R. Zahler, X. Wang, J. Thottathil, J. C. Barrish and R. P. Polniaszek, Tetrahedron Lett., 1997, 38, 3175-3187; (i) J. Barluenga, B. Baragana, A. Alonso and J. M. Concellon, J. Chem. Soc., Chem. Commun., 1994, 969-970.
22. For synthetic approaches to halomethyl ketones, see: (a) D. P. Getman, G. A. DeCrescenzo, R. M. Heintz, K. L. Reed, J. J. Talley, M. L. Bryant, M. Clare, K. A. Houseman, J. Marr, R. A. Mueller, M. L. Vazques, H.-S. Shieh, W. C. Stallings and R. A. Stegeman, J. Med. Chem., 1993, 36, 288-291; (b) P. Raddatz, A. Jonczyk, K.-O. Minck, C. J. Schmitges and J. Sombroek, J. Med. Chem., 1991, 34, 3267-3280; (c) L. E. Fisher and J. M. Muchowski, Org. Prep. Proc. Int., 1990, 22, 399-484; (d) A. Heinsoo, G. Raidaru, K. Linask, J. Jarv, M. Zetterstrom and U. Langel, Tetrahedron: Asymmetry, 1995, 6, 2245-2247; (e) B. K. Handa, P. J. Machin, J. A. Martin, S. Redshaw and G. J. Thomas, F. Hoffmann La Roche AG, Eur. Pat. Appl., EP346847, 1989; (f) A. Albeck and R. Persky, Tetrahedron, 1994, 50, 6333-6346; (g) A. Nishiyama, T. Sugawa, H. Manabe, K. Inoue and N. Yoshida, Kaneka Corp., U.S. Patent 5 929 284, 1999; (h) P. Chen, P. T. W. Cheng, S. H. Spergel, R. Zahler, X. Wang, J. Thottathil, J. C. Barrish and R. P. Polniaszek, Tetrahedron Lett., 1997, 38, 3175-3187; (i) J. Barluenga, B. Baragana, A. Alonso and J. M. Concellon, J. Chem. Soc., Chem. Commun., 1994, 969-970.
23. For synthetic approaches to halomethyl ketones, see: (a) D. P. Getman, G. A. DeCrescenzo, R. M. Heintz, K. L. Reed, J. J. Talley, M. L. Bryant, M. Clare, K. A. Houseman, J. Marr, R. A. Mueller, M. L. Vazques, H.-S. Shieh, W. C. Stallings and R. A. Stegeman, J. Med. Chem., 1993, 36, 288-291; (b) P. Raddatz, A. Jonczyk, K.-O. Minck, C. J. Schmitges and J. Sombroek, J. Med. Chem., 1991, 34, 3267-3280; (c) L. E. Fisher and J. M. Muchowski, Org. Prep. Proc. Int., 1990, 22, 399-484; (d) A. Heinsoo, G. Raidaru, K. Linask, J. Jarv, M. Zetterstrom and U. Langel, Tetrahedron: Asymmetry, 1995, 6, 2245-2247; (e) B. K. Handa, P. J. Machin, J. A. Martin, S. Redshaw and G. J. Thomas, F. Hoffmann La Roche AG, Eur. Pat. Appl., EP346847, 1989; (f) A. Albeck and R. Persky, Tetrahedron, 1994, 50, 6333-6346; (g) A. Nishiyama, T. Sugawa, H. Manabe, K. Inoue and N. Yoshida, Kaneka Corp., U.S. Patent 5 929 284, 1999; (h) P. Chen, P. T. W. Cheng, S. H. Spergel, R. Zahler, X. Wang, J. Thottathil, J. C. Barrish and R. P. Polniaszek, Tetrahedron Lett., 1997, 38, 3175-3187; (i) J. Barluenga, B. Baragana, A. Alonso and J. M. Concellon, J. Chem. Soc., Chem. Commun., 1994, 969-970.
24. For synthetic approaches to halomethyl ketones, see: (a) D. P. Getman, G. A. DeCrescenzo, R. M. Heintz, K. L. Reed, J. J. Talley, M. L. Bryant, M. Clare, K. A. Houseman, J. Marr, R. A. Mueller, M. L. Vazques, H.-S. Shieh, W. C. Stallings and R. A. Stegeman, J. Med. Chem., 1993, 36, 288-291; (b) P. Raddatz, A. Jonczyk, K.-O. Minck, C. J. Schmitges and J. Sombroek, J. Med. Chem., 1991, 34, 3267-3280; (c) L. E. Fisher and J. M. Muchowski, Org. Prep. Proc. Int., 1990, 22, 399-484; (d) A. Heinsoo, G. Raidaru, K. Linask, J. Jarv, M. Zetterstrom and U. Langel, Tetrahedron: Asymmetry, 1995, 6, 2245-2247; (e) B. K. Handa, P. J. Machin, J. A. Martin, S. Redshaw and G. J. Thomas, F. Hoffmann La Roche AG, Eur. Pat. Appl., EP346847, 1989; (f) A. Albeck and R. Persky, Tetrahedron, 1994, 50, 6333-6346; (g) A. Nishiyama, T. Sugawa, H. Manabe, K. Inoue and N. Yoshida, Kaneka Corp., U.S. Patent 5 929 284, 1999; (h) P. Chen, P. T. W. Cheng, S. H. Spergel, R. Zahler, X. Wang, J. Thottathil, J. C. Barrish and R. P. Polniaszek, Tetrahedron Lett., 1997, 38, 3175-3187; (i) J. Barluenga, B. Baragana, A. Alonso and J. M. Concellon, J. Chem. Soc., Chem. Commun., 1994, 969-970.
25. For synthetic approaches to halomethyl ketones, see: (a) D. P. Getman, G. A. DeCrescenzo, R. M. Heintz, K. L. Reed, J. J. Talley, M. L. Bryant, M. Clare, K. A. Houseman, J. Marr, R. A. Mueller, M. L. Vazques, H.-S. Shieh, W. C. Stallings and R. A. Stegeman, J. Med. Chem., 1993, 36, 288-291; (b) P. Raddatz, A. Jonczyk, K.-O. Minck, C. J. Schmitges and J. Sombroek, J. Med. Chem., 1991, 34, 3267-3280; (c) L. E. Fisher and J. M. Muchowski, Org. Prep. Proc. Int., 1990, 22, 399-484; (d) A. Heinsoo, G. Raidaru, K. Linask, J. Jarv, M. Zetterstrom and U. Langel, Tetrahedron: Asymmetry, 1995, 6, 2245-2247; (e) B. K. Handa, P. J. Machin, J. A. Martin, S. Redshaw and G. J. Thomas, F. Hoffmann La Roche AG, Eur. Pat. Appl., EP346847, 1989; (f) A. Albeck and R. Persky, Tetrahedron, 1994, 50, 6333-6346; (g) A. Nishiyama, T. Sugawa, H. Manabe, K. Inoue and N. Yoshida, Kaneka Corp., U.S. Patent 5 929 284, 1999; (h) P. Chen, P. T. W. Cheng, S. H. Spergel, R. Zahler, X. Wang, J. Thottathil, J. C. Barrish and R. P. Polniaszek, Tetrahedron Lett., 1997, 38, 3175-3187; (i) J. Barluenga, B. Baragana, A. Alonso and J. M. Concellon, J. Chem. Soc., Chem. Commun., 1994, 969-970.
26. For synthetic approaches to halomethyl ketones, see: (a) D. P. Getman, G. A. DeCrescenzo, R. M. Heintz, K. L. Reed, J. J. Talley, M. L. Bryant, M. Clare, K. A. Houseman, J. Marr, R. A. Mueller, M. L. Vazques, H.-S. Shieh, W. C. Stallings and R. A. Stegeman, J. Med. Chem., 1993, 36, 288-291; (b) P. Raddatz, A. Jonczyk, K.-O. Minck, C. J. Schmitges and J. Sombroek, J. Med. Chem., 1991, 34, 3267-3280; (c) L. E. Fisher and J. M. Muchowski, Org. Prep. Proc. Int., 1990, 22, 399-484; (d) A. Heinsoo, G. Raidaru, K. Linask, J. Jarv, M. Zetterstrom and U. Langel, Tetrahedron: Asymmetry, 1995, 6, 2245-2247; (e) B. K. Handa, P. J. Machin, J. A. Martin, S. Redshaw and G. J. Thomas, F. Hoffmann La Roche AG, Eur. Pat. Appl., EP346847, 1989; (f) A. Albeck and R. Persky, Tetrahedron, 1994, 50, 6333-6346; (g) A. Nishiyama, T. Sugawa, H. Manabe, K. Inoue and N. Yoshida, Kaneka Corp., U.S. Patent 5 929 284, 1999; (h) P. Chen, P. T. W. Cheng, S. H. Spergel, R. Zahler, X. Wang, J. Thottathil, J. C. Barrish and R. P. Polniaszek, Tetrahedron Lett., 1997, 38, 3175-3187; (i) J. Barluenga, B. Baragana, A. Alonso and J. M. Concellon, J. Chem. Soc., Chem. Commun., 1994, 969-970.
27. For the chloromethylation of amino acid derivatives recently reported by our group, see: (a) T. Onishi, N. Hirose, T. Nakano, M. Nakazawa and K. Izawa, Tetrahedron Lett., 2001, 42, 5883-5885; (b) T. Onishi, T. Nakano, N. Hirose, M. Nakazawa and K. Izawa, Tetrahedron Lett., 2001, 42, 6337-6340.
28. For the chloromethylation of amino acid derivatives recently reported by our group, see: (a) T. Onishi, N. Hirose, T. Nakano, M. Nakazawa and K. Izawa, Tetrahedron Lett., 2001, 42, 5883-5885; (b) T. Onishi, T. Nakano, N. Hirose, M. Nakazawa and K. Izawa, Tetrahedron Lett., 2001, 42, 6337-6340.
29. Y. Honda, S. Katayama, M. Kojima, T. Suzuki and K. Izawa, Tetrahedron Lett., 2003, 44, 3163-3166.
30. For the general synthesis of β-ketoesters via activation of carbonyl, see: (a) R. V. Hoffman and J. Tao, J. Org. Chem., 1997, 62, 2292-2297; (b) R. V. Hoffman and H. Kim, Tetrahedron Lett., 1992, 25, 3579-3582; (c) R. V. Hoffman, W. S. Weiner and N. Maslouh, J. Org. Chem., 2001, 66, 5790-5795.
31. For the general synthesis of β-ketoesters via activation of carbonyl, see: (a) R. V. Hoffman and J. Tao, J. Org. Chem., 1997, 62, 2292-2297; (b) R. V. Hoffman and H. Kim, Tetrahedron Lett., 1992, 25, 3579-3582; (c) R. V. Hoffman, W. S. Weiner and N. Maslouh, J. Org. Chem., 2001, 66, 5790-5795.
32. For the general synthesis of β-ketoesters via activation of carbonyl, see: (a) R. V. Hoffman and J. Tao, J. Org. Chem., 1997, 62, 2292-2297; (b) R. V. Hoffman and H. Kim, Tetrahedron Lett., 1992, 25, 3579-3582; (c) R. V. Hoffman, W. S. Weiner and N. Maslouh, J. Org. Chem., 2001, 66, 5790-5795.
33. (a) Y. Honda, S. Katayama, M. Kojima, T. Suzuki and K. Izawa, Org. Lett., 2002, 4, 447-449;
34. (b) Y. Honda, S. Katayama, K. Izawa, M. Nakazawa, T. Suzuki and K. Kanno, Ajinomoto Co., Inc., Eur. Pat. Appl., EP0774453, May 21, 1997;
35. (c) Y. Honda, S. Katayama, K. Izawa, M. Nakazawa, T. Suzuki and N. Kanno, Ajinomoto Co., Inc., U.S. Patent 5 902 887, May 11, 1999.
36. (a) H. C. Brown, J. V. N. Vara Prasad and M. Zaidlewicz, J. Org. Chem., 1988, 53, 2911-2916;
37. (b) A. Schnyder, A. Togni and O. Werbitzky, Lonza A. G., Ger. Offen., DE19807330, 1998.
38. Y. Uozumi and T. Hayashi, Tetrahedron Lett., 1993, 34, 2335-2338.
39. (a) Y. Yuasa and H. Tsuruta, Liebigs Ann. Chem., 1997, 1877-1879;
40. (b) K. Kinoshita, T. Moroshima, Y. Yanagida, N. Nagashima, Y. Saka, T. Honda, Y. Fuse and Y. Ueda, Kaneka Corp., PCT Int. Appl., WO0063199, 2000.
41. (a) F. Nomoto, N. Shirasaka and K. Otsuka, Nagase and Co., Ltd., Japan Kokai Tokkyo Koho, JP10337197, 1998;
42. (b) M. Baumann, B. H. Hauer and U. T. Bornscheuer, Tetrahedron: Asymmetry, 2000, 11, 4781-4790.
43. V. K. Tandon, A. M. van Leusen and H. Wynberg, J. Org. Chem., 1983, 48, 2767-2769.
44. (a) H. Hayashi, K. Nakanishi, C. Brandon and J. Marmur, J. Am. Chem. Soc., 1973, 95, 8749-8757;
45. (b) S. Cicchi, A. Goti and A. Brandi, J. Org. Chem., 1995, 60, 4743-4748.
46. For a reaction modified from the original method reported in the literature, see: K. Bischofberger and J. R. Bull, Tetrahedron, 1985, 41, 365-374.
47. For derivatization to MTPA ester, see: (a) J. A. Dale, D. L. Dull and H. S. Mosher, J. Org. Chem., 1969, 34, 2543-2549; (b) S. Yamaguchi, in Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, New York, 1983, vol. 1, p. 128.
48. For derivatization to MTPA ester, see: (a) J. A. Dale, D. L. Dull and H. S. Mosher, J. Org. Chem., 1969, 34, 2543-2549; (b) S. Yamaguchi, in Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, New York, 1983, vol. 1, p. 128.
49. 20 +17.638 (2.40, MeOH) (measured).
50. (a) A. Albeck and Persky, Tetrahedron, 1994, 50, 6333-6346;
51. (b) M.-N. Dufour, P. Jouin, J. Poncet, A. Pantaloni and B. Castro, J. Chem. Soc., Perkin Trans. 1, 1986, 1895-1899;
52. (c) P. Chen, P. T. W. Cheng, S. H. Spergel, J. C. Barrish, J. K. Thottathil, P. P. Zahler, P. Richard and X. Wang, Bristol-Myers Squibb Co., U.S. Patent 5 481 011, 1996;
53. (d) D. P. Rotella, Tetrahedron Lett., 1995, 36, 5453-5456.
54. For the preparation of chloroformate from alcohol with triphosgene, see: H. Eckert and B. Forster, Angew. Chem., Int. Ed. Engl., 1981, 26, 894-895.