A novel and efficient synthesis of a highly active analogue of clasto- lactacystin β-lactone

Journal of the American Chemical Society

Volumn 121, Issue 43, 1999, Pages 9967-9976

  Soucy, François ^a   Grenier, Louis ^a   Behnke, Mark L ^a   Destree, Antonia T ^a   McCormack, Teresa A ^a   Adams, Julian ^a   Plamondon, Louis ^a,b  

^a MILLENNIUM PHARMACEUTICALS INC   (United States)

^b BASF Bioresearch Corporation   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; LACTACYSTIN; LACTONE; OXAZOLINE DERIVATIVE;

ARTICLE; CHELATION; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0033520753     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991175f     Document Type: Article

References (95)

1. Reviews: (a) Goldberg, A. L.; Stein, R. L.; Adams, J. Chem. Biol. 1995, 2, 503. (b) Coux, O.; Tanaka, K.; Goldberg, A. L. Annu. Rev. Biochem. 1996, 65, 801. (c) Deshaies, R. J. Trends Cell Biol. 1995, 5, 428. (d) Rubin, D.; Finley, D. M. Curr. Biol. 1995, 3, 854. (e) Tanaka, K. Mol. Biol. Rep. 1995, 21, 21. (f) Ciechanover, A. Cell 1994, 79, 13. (g) Peters, J. M. Trends Biochem. Sci. 1994, 19, 377. (h) Wilk, S. Enzyme Protein 1993, 47, 187. (i) Rivett, A. J. Biochem. J. 1993, 291, 1.
2. Reviews: (a) Goldberg, A. L.; Stein, R. L.; Adams, J. Chem. Biol. 1995, 2, 503. (b) Coux, O.; Tanaka, K.; Goldberg, A. L. Annu. Rev. Biochem. 1996, 65, 801. (c) Deshaies, R. J. Trends Cell Biol. 1995, 5, 428. (d) Rubin, D.; Finley, D. M. Curr. Biol. 1995, 3, 854. (e) Tanaka, K. Mol. Biol. Rep. 1995, 21, 21. (f) Ciechanover, A. Cell 1994, 79, 13. (g) Peters, J. M. Trends Biochem. Sci. 1994, 19, 377. (h) Wilk, S. Enzyme Protein 1993, 47, 187. (i) Rivett, A. J. Biochem. J. 1993, 291, 1.
3. Reviews: (a) Goldberg, A. L.; Stein, R. L.; Adams, J. Chem. Biol. 1995, 2, 503. (b) Coux, O.; Tanaka, K.; Goldberg, A. L. Annu. Rev. Biochem. 1996, 65, 801. (c) Deshaies, R. J. Trends Cell Biol. 1995, 5, 428. (d) Rubin, D.; Finley, D. M. Curr. Biol. 1995, 3, 854. (e) Tanaka, K. Mol. Biol. Rep. 1995, 21, 21. (f) Ciechanover, A. Cell 1994, 79, 13. (g) Peters, J. M. Trends Biochem. Sci. 1994, 19, 377. (h) Wilk, S. Enzyme Protein 1993, 47, 187. (i) Rivett, A. J. Biochem. J. 1993, 291, 1.
4. Reviews: (a) Goldberg, A. L.; Stein, R. L.; Adams, J. Chem. Biol. 1995, 2, 503. (b) Coux, O.; Tanaka, K.; Goldberg, A. L. Annu. Rev. Biochem. 1996, 65, 801. (c) Deshaies, R. J. Trends Cell Biol. 1995, 5, 428. (d) Rubin, D.; Finley, D. M. Curr. Biol. 1995, 3, 854. (e) Tanaka, K. Mol. Biol. Rep. 1995, 21, 21. (f) Ciechanover, A. Cell 1994, 79, 13. (g) Peters, J. M. Trends Biochem. Sci. 1994, 19, 377. (h) Wilk, S. Enzyme Protein 1993, 47, 187. (i) Rivett, A. J. Biochem. J. 1993, 291, 1.
5. Reviews: (a) Goldberg, A. L.; Stein, R. L.; Adams, J. Chem. Biol. 1995, 2, 503. (b) Coux, O.; Tanaka, K.; Goldberg, A. L. Annu. Rev. Biochem. 1996, 65, 801. (c) Deshaies, R. J. Trends Cell Biol. 1995, 5, 428. (d) Rubin, D.; Finley, D. M. Curr. Biol. 1995, 3, 854. (e) Tanaka, K. Mol. Biol. Rep. 1995, 21, 21. (f) Ciechanover, A. Cell 1994, 79, 13. (g) Peters, J. M. Trends Biochem. Sci. 1994, 19, 377. (h) Wilk, S. Enzyme Protein 1993, 47, 187. (i) Rivett, A. J. Biochem. J. 1993, 291, 1.
6. Reviews: (a) Goldberg, A. L.; Stein, R. L.; Adams, J. Chem. Biol. 1995, 2, 503. (b) Coux, O.; Tanaka, K.; Goldberg, A. L. Annu. Rev. Biochem. 1996, 65, 801. (c) Deshaies, R. J. Trends Cell Biol. 1995, 5, 428. (d) Rubin, D.; Finley, D. M. Curr. Biol. 1995, 3, 854. (e) Tanaka, K. Mol. Biol. Rep. 1995, 21, 21. (f) Ciechanover, A. Cell 1994, 79, 13. (g) Peters, J. M. Trends Biochem. Sci. 1994, 19, 377. (h) Wilk, S. Enzyme Protein 1993, 47, 187. (i) Rivett, A. J. Biochem. J. 1993, 291, 1.
7. Reviews: (a) Goldberg, A. L.; Stein, R. L.; Adams, J. Chem. Biol. 1995, 2, 503. (b) Coux, O.; Tanaka, K.; Goldberg, A. L. Annu. Rev. Biochem. 1996, 65, 801. (c) Deshaies, R. J. Trends Cell Biol. 1995, 5, 428. (d) Rubin, D.; Finley, D. M. Curr. Biol. 1995, 3, 854. (e) Tanaka, K. Mol. Biol. Rep. 1995, 21, 21. (f) Ciechanover, A. Cell 1994, 79, 13. (g) Peters, J. M. Trends Biochem. Sci. 1994, 19, 377. (h) Wilk, S. Enzyme Protein 1993, 47, 187. (i) Rivett, A. J. Biochem. J. 1993, 291, 1.
8. Reviews: (a) Goldberg, A. L.; Stein, R. L.; Adams, J. Chem. Biol. 1995, 2, 503. (b) Coux, O.; Tanaka, K.; Goldberg, A. L. Annu. Rev. Biochem. 1996, 65, 801. (c) Deshaies, R. J. Trends Cell Biol. 1995, 5, 428. (d) Rubin, D.; Finley, D. M. Curr. Biol. 1995, 3, 854. (e) Tanaka, K. Mol. Biol. Rep. 1995, 21, 21. (f) Ciechanover, A. Cell 1994, 79, 13. (g) Peters, J. M. Trends Biochem. Sci. 1994, 19, 377. (h) Wilk, S. Enzyme Protein 1993, 47, 187. (i) Rivett, A. J. Biochem. J. 1993, 291, 1.
9. Reviews: (a) Goldberg, A. L.; Stein, R. L.; Adams, J. Chem. Biol. 1995, 2, 503. (b) Coux, O.; Tanaka, K.; Goldberg, A. L. Annu. Rev. Biochem. 1996, 65, 801. (c) Deshaies, R. J. Trends Cell Biol. 1995, 5, 428. (d) Rubin, D.; Finley, D. M. Curr. Biol. 1995, 3, 854. (e) Tanaka, K. Mol. Biol. Rep. 1995, 21, 21. (f) Ciechanover, A. Cell 1994, 79, 13. (g) Peters, J. M. Trends Biochem. Sci. 1994, 19, 377. (h) Wilk, S. Enzyme Protein 1993, 47, 187. (i) Rivett, A. J. Biochem. J. 1993, 291, 1.
10. (a) Rock, K. L.; Gramm, C.; Rothstein, L.; Clark, K.; Stein, R.; Dick, L.; Hwang, D.; Goldberg, A. L. Cell 1994, 78, 761.
11. (b) King, R. W.; Deshaies, R. J.; Peters, J.-M.; Kirschner, M. W. Science 1996, 78, 761.
12. (a) Barnes, P. J.; Karin, M. News Eng. J. Med. 1997, 336, 1066.
13. (b) Baldwin, A. S. Annu. Rev. Immunol. 1996, 14, 649.
14. (c) Thanos, D.; Maniatis, T. Cell 1995, 80, 529.
15. (d) Grilli, M.; Chiu, J. J.-S.; Leonardo, M. J. Int. Rev. Cytol. 1993, 143, 1.
16. (e) Baeuerle, P. A.; Baltimore, D. Cell 1996, 87, 13.
17. (a) Palombella, V. J.; Conner, E. M.; Fuseler, J. W.; Destree, A. D.; Davis, J. M.; Laroux, F. S.; Wolf, R. E.; Huang, J.; Brand, S.; Elliott, P. E.; Lazarus, D.; McCormack, T.; Parent, L.; Stein, R.; Adams, J.; Grisham, M. B. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 15671.
18. (b) Campbell, B.; Adams, J.; Shin, Y. K.; Lefer, A. M. J. Mol. Cell Cardiol. 1999, 31, 467
19. (c) Elliott, P. J.; Pien, C. S.; McCormack, T. A.; Chapman, I. D.; Adams, J. J. Allergy Clin. Immunol., in press.
20. (d) Vanderlugt, C. L.; Rahbe, S. M.; Elliott, P. J.; Dal Canto, M. C.; Miller, S. D. J. Neuroimmunol., in press.
21. (e) Phillips, J. B.; Williams, A. J.; Elliott, P. E.; Tortella, F. C. FASEB 1999, 13, A1099 (abstract no. 817.3).
22. (f) Phillips, J. B.; Williams, A. J.; Elliott, P. E.; Tortella, F. C. J. Neurol. 1998, 24, 215 (abstract no. 86.11).
23. (a) Ōmura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113.
24. (b) Ōmura, S.; Matsuzaki, K.; Fujimoto, T.; Kosuge, K.; Furuya, T.; Fujita, S.; Nakagawa, A. J. Antibiot. 1991, 44, 117. Also see:
25. (c) Nakagawa, A.; Takahashi, S.; Uchida, K.; Matsuzaki, K.; Omura, S.; Nakamura, A.; Kurihara, N.; Nakamatsu, T.; Miyake, Y.; Take, K.; Kainosho, M. Tetrahedron Lett. 1994, 35, 5009.
26. For a review on microbial metabolites, see: Ōmura, S. Gene 1992, 115, 141.
27. (a) Fenteany, G.; Standaert, R. F.; Reichard, G. A.; Corey, E. J.; Schreiber, S. L. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 3358.
28. (b) Fenteany, G.; Standaert, R. F.; Lane, W. S.; Choi, S.; Corey, E. J.; Schreiber, S. L. Science 1995, 268, 726.
29. Craiu, A.; Gaczynska, M.; Akopian, T.; Gramm, C. F.; Fenteany, G.; Goldberg, A. L.; Rock, K. L. J. Biol. Chem. 1997, 272, 13437.
30. (a) Dick, L. R.; Cruikshank, A. A.; Grenier, L.; Melandri, F. D.; Nunes, S. L.; Palombella, V. J.; Parent, L. A.; Plamondon, L.; Stein, R. L. J. biol. Chem. 1997, 272, 182.
31. (b) Dick, L. R.; Cruikshank, A. A.; Destree, A. T.; Grenier, L.; McCormack, T. A.; Melandri, F. D.; Nunes, S. L.; Stein, R. L. J. Biol. Chem. 1996, 271, 7273.
32. Groll, M.; Ditzel, L.; Löwe, J.; Stock, D.; Bochtler, M.; Bartunik, H. D.; Huber, R. Nature 1997, 386, 463.
33. (a) Corey, E. J.; Reichard, G. A. J. Am. Chem. Soc. 1992, 114, 10677.
34. (b) Corey, E. J.; Reichard, G. A.; Kania, R. Tetrahedron Lett. 1993, 34, 6977.
35. (c) Corey, E. J.; Li, W.; Reichard, G. A. J. Am. Chem. Soc. 1998, 120, 2330.
36. (d) Sunazuka, T.; Nagamitsu, K.; Matsuzaki, K.; Tanaka, H.; Omura, S.; Smith, A. B., III. J. Am. Chem. Soc. 1993, 115, 5302.
37. (e) Nagamitsu, K.; Sunazuka, T.; Tanaka, H.; Ōmura, S.; Sprengeler, P. A.; Smith, A. B., III. J. Am. Chem. Soc. 1996, 118, 3584.
38. (f) Uno, H.; Baldwin, J. E.; Russell, A. T. J. Am. Chem. Soc. 1994, 116, 2139.
39. (g) Chida, N.; Takeoka, J.; Tsunimi, N.; Ogaa, S. J. Chem. Soc., Chem. Commun. 1995, 793.
40. (h) Corey, E. J.; Li, W.; Nagamitsu, T. Angew. Chem., Int. Ed. 1998, 37, 1676.
41. (i) Kang, S. H.; Jun, H.-S. J. Chem. Soc., Chem. Commun. 1998, 1929.
42. (j) Corey, E. J.; Reichard, G. A. Tetrahedron Lett. 1993, 34, 6973.
43. For enantioselective syntheses of analogues of lactacystin and lactacystin β-lactone, see: (a) Corey, E. J.; Li, W.-D. Z.; Nagamitsu, T.; Fenteany, G. Tetrahedron 1999, 55, 3305. (b) Corey, E. J.; Li, W.-D. Z. Tetrahedron Lett. 1998, 39, 7475. (c) Corey, E. J.; Li, W.-D. Z. Tetrahedron Lett. 1998, 39, 8043. (d) Corey, E. J.; Reichard, G. A. Tetrahedron Lett. 1993, 34, 6973. (e) Corey, E. J.; Choi, S. Tetrahedron Lett. 1993, 34, 6969. Also see ref 11b.
44. For enantioselective syntheses of analogues of lactacystin and lactacystin β-lactone, see: (a) Corey, E. J.; Li, W.-D. Z.; Nagamitsu, T.; Fenteany, G. Tetrahedron 1999, 55, 3305. (b) Corey, E. J.; Li, W.-D. Z. Tetrahedron Lett. 1998, 39, 7475. (c) Corey, E. J.; Li, W.-D. Z. Tetrahedron Lett. 1998, 39, 8043. (d) Corey, E. J.; Reichard, G. A. Tetrahedron Lett. 1993, 34, 6973. (e) Corey, E. J.; Choi, S. Tetrahedron Lett. 1993, 34, 6969. Also see ref 11b.
45. For enantioselective syntheses of analogues of lactacystin and lactacystin β-lactone, see: (a) Corey, E. J.; Li, W.-D. Z.; Nagamitsu, T.; Fenteany, G. Tetrahedron 1999, 55, 3305. (b) Corey, E. J.; Li, W.-D. Z. Tetrahedron Lett. 1998, 39, 7475. (c) Corey, E. J.; Li, W.-D. Z. Tetrahedron Lett. 1998, 39, 8043. (d) Corey, E. J.; Reichard, G. A. Tetrahedron Lett. 1993, 34, 6973. (e) Corey, E. J.; Choi, S. Tetrahedron Lett. 1993, 34, 6969. Also see ref 11b.
46. For enantioselective syntheses of analogues of lactacystin and lactacystin β-lactone, see: (a) Corey, E. J.; Li, W.-D. Z.; Nagamitsu, T.; Fenteany, G. Tetrahedron 1999, 55, 3305. (b) Corey, E. J.; Li, W.-D. Z. Tetrahedron Lett. 1998, 39, 7475. (c) Corey, E. J.; Li, W.-D. Z. Tetrahedron Lett. 1998, 39, 8043. (d) Corey, E. J.; Reichard, G. A. Tetrahedron Lett. 1993, 34, 6973. (e) Corey, E. J.; Choi, S. Tetrahedron Lett. 1993, 34, 6969. Also see ref 11b.
47. For enantioselective syntheses of analogues of lactacystin and lactacystin β-lactone, see: (a) Corey, E. J.; Li, W.-D. Z.; Nagamitsu, T.; Fenteany, G. Tetrahedron 1999, 55, 3305. (b) Corey, E. J.; Li, W.-D. Z. Tetrahedron Lett. 1998, 39, 7475. (c) Corey, E. J.; Li, W.-D. Z. Tetrahedron Lett. 1998, 39, 8043. (d) Corey, E. J.; Reichard, G. A. Tetrahedron Lett. 1993, 34, 6973. (e) Corey, E. J.; Choi, S. Tetrahedron Lett. 1993, 34, 6969. Also see ref 11b.
48. Those findings will be reported elsewhere. For a review on the biological activity of analogues of lactacystin and the related β-lactone, see: Corey, E. J.; Li, W.-D. Z. Chem. Pharm. Bull. 1999, 47, 1.
49. Similar findings have been reported by Corey et al.; see refs 12a and 12b.
50. An elegant Mukaiyama aldol coupling strategy has recently been reported by Corey in which an anti aldol product is formed in ca. 90% de and transformed in seven steps into lactacystin 1 (ref 11c). Corey and Choi have also used a syn-selective aldol route to prepare the inactive 6R diastereomer of lactacystin, which is incapable of forming the β-lactone (ref 12b).
51. It should be noted that the absolute configuration of unichiral center C5 in oxazoline 6 is a priori unimportant because this center undergoes pyramidalization during enolization.
52. For the preparation of enantiomerically pure (2S,3S)- or (2R,3R)-3-hydroxyleucine, see: (a) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181. (b) Caldwell, G. C.; Bondy, S. S. Synthesis 1990, 34. Also see: (c) Sunazuka, T.; Nagamitsu, T.; Tanaka, H.; Sprengeler, P. A.; Smith, A. B., III; Ōmura, S. Tetrahedron Lett. 1993, 34, 4447. (d) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (e) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799. (f) Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869. (g) Blaser, D.; Seebach, D. Liebigs Ann. Chem. 1991, 1067. (h) Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C.; Webber, T. Helv. Chim. Acta 1987, 70, 2037. (i) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39. (j) Reno, D. S.; Lotz, B. T.; Miller, M. J. Tetrahedron Lett. 1990, 31, 827. (k) Williams, R. M.; Im, M.-N.; Cao, J. J. Am. Chem. Soc. 1991, 113, 6976. (l) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. (m) Genet, J. P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. (n) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. (o) Suga, H.; Shi, X.; Ibata, T. J. Org. Chem. 1993, 58, 7397. (p) Horikawa, M. H.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
53. For the preparation of enantiomerically pure (2S,3S)- or (2R,3R)- 3-hydroxyleucine, see: (a) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181. (b) Caldwell, G. C.; Bondy, S. S. Synthesis 1990, 34. Also see: (c) Sunazuka, T.; Nagamitsu, T.; Tanaka, H.; Sprengeler, P. A.; Smith, A. B., III; Ōmura, S. Tetrahedron Lett. 1993, 34, 4447. (d) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (e) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799. (f) Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869. (g) Blaser, D.; Seebach, D. Liebigs Ann. Chem. 1991, 1067. (h) Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C.; Webber, T. Helv. Chim. Acta 1987, 70, 2037. (i) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39. (j) Reno, D. S.; Lotz, B. T.; Miller, M. J. Tetrahedron Lett. 1990, 31, 827. (k) Williams, R. M.; Im, M.-N.; Cao, J. J. Am. Chem. Soc. 1991, 113, 6976. (l) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. (m) Genet, J. P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. (n) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. (o) Suga, H.; Shi, X.; Ibata, T. J. Org. Chem. 1993, 58, 7397. (p) Horikawa, M. H.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
54. For the preparation of enantiomerically pure (2S,3S)- or (2R,3R)- 3-hydroxyleucine, see: (a) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181. (b) Caldwell, G. C.; Bondy, S. S. Synthesis 1990, 34. Also see: (c) Sunazuka, T.; Nagamitsu, T.; Tanaka, H.; Sprengeler, P. A.; Smith, A. B., III; Ōmura, S. Tetrahedron Lett. 1993, 34, 4447. (d) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (e) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799. (f) Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869. (g) Blaser, D.; Seebach, D. Liebigs Ann. Chem. 1991, 1067. (h) Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C.; Webber, T. Helv. Chim. Acta 1987, 70, 2037. (i) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39. (j) Reno, D. S.; Lotz, B. T.; Miller, M. J. Tetrahedron Lett. 1990, 31, 827. (k) Williams, R. M.; Im, M.-N.; Cao, J. J. Am. Chem. Soc. 1991, 113, 6976. (l) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. (m) Genet, J. P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. (n) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. (o) Suga, H.; Shi, X.; Ibata, T. J. Org. Chem. 1993, 58, 7397. (p) Horikawa, M. H.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
55. For the preparation of enantiomerically pure (2S,3S)- or (2R,3R)- 3-hydroxyleucine, see: (a) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181. (b) Caldwell, G. C.; Bondy, S. S. Synthesis 1990, 34. Also see: (c) Sunazuka, T.; Nagamitsu, T.; Tanaka, H.; Sprengeler, P. A.; Smith, A. B., III; Ōmura, S. Tetrahedron Lett. 1993, 34, 4447. (d) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (e) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799. (f) Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869. (g) Blaser, D.; Seebach, D. Liebigs Ann. Chem. 1991, 1067. (h) Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C.; Webber, T. Helv. Chim. Acta 1987, 70, 2037. (i) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39. (j) Reno, D. S.; Lotz, B. T.; Miller, M. J. Tetrahedron Lett. 1990, 31, 827. (k) Williams, R. M.; Im, M.-N.; Cao, J. J. Am. Chem. Soc. 1991, 113, 6976. (l) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. (m) Genet, J. P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. (n) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. (o) Suga, H.; Shi, X.; Ibata, T. J. Org. Chem. 1993, 58, 7397. (p) Horikawa, M. H.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
56. For the preparation of enantiomerically pure (2S,3S)- or (2R,3R)- 3-hydroxyleucine, see: (a) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181. (b) Caldwell, G. C.; Bondy, S. S. Synthesis 1990, 34. Also see: (c) Sunazuka, T.; Nagamitsu, T.; Tanaka, H.; Sprengeler, P. A.; Smith, A. B., III; Ōmura, S. Tetrahedron Lett. 1993, 34, 4447. (d) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (e) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799. (f) Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869. (g) Blaser, D.; Seebach, D. Liebigs Ann. Chem. 1991, 1067. (h) Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C.; Webber, T. Helv. Chim. Acta 1987, 70, 2037. (i) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39. (j) Reno, D. S.; Lotz, B. T.; Miller, M. J. Tetrahedron Lett. 1990, 31, 827. (k) Williams, R. M.; Im, M.-N.; Cao, J. J. Am. Chem. Soc. 1991, 113, 6976. (l) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. (m) Genet, J. P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. (n) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. (o) Suga, H.; Shi, X.; Ibata, T. J. Org. Chem. 1993, 58, 7397. (p) Horikawa, M. H.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
57. For the preparation of enantiomerically pure (2S,3S)- or (2R,3R)- 3-hydroxyleucine, see: (a) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181. (b) Caldwell, G. C.; Bondy, S. S. Synthesis 1990, 34. Also see: (c) Sunazuka, T.; Nagamitsu, T.; Tanaka, H.; Sprengeler, P. A.; Smith, A. B., III; Ōmura, S. Tetrahedron Lett. 1993, 34, 4447. (d) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (e) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799. (f) Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869. (g) Blaser, D.; Seebach, D. Liebigs Ann. Chem. 1991, 1067. (h) Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C.; Webber, T. Helv. Chim. Acta 1987, 70, 2037. (i) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39. (j) Reno, D. S.; Lotz, B. T.; Miller, M. J. Tetrahedron Lett. 1990, 31, 827. (k) Williams, R. M.; Im, M.-N.; Cao, J. J. Am. Chem. Soc. 1991, 113, 6976. (l) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. (m) Genet, J. P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. (n) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. (o) Suga, H.; Shi, X.; Ibata, T. J. Org. Chem. 1993, 58, 7397. (p) Horikawa, M. H.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
58. For the preparation of enantiomerically pure (2S,3S)- or (2R,3R)- 3-hydroxyleucine, see: (a) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181. (b) Caldwell, G. C.; Bondy, S. S. Synthesis 1990, 34. Also see: (c) Sunazuka, T.; Nagamitsu, T.; Tanaka, H.; Sprengeler, P. A.; Smith, A. B., III; Ōmura, S. Tetrahedron Lett. 1993, 34, 4447. (d) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (e) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799. (f) Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869. (g) Blaser, D.; Seebach, D. Liebigs Ann. Chem. 1991, 1067. (h) Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C.; Webber, T. Helv. Chim. Acta 1987, 70, 2037. (i) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39. (j) Reno, D. S.; Lotz, B. T.; Miller, M. J. Tetrahedron Lett. 1990, 31, 827. (k) Williams, R. M.; Im, M.-N.; Cao, J. J. Am. Chem. Soc. 1991, 113, 6976. (l) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. (m) Genet, J. P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. (n) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. (o) Suga, H.; Shi, X.; Ibata, T. J. Org. Chem. 1993, 58, 7397. (p) Horikawa, M. H.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
59. For the preparation of enantiomerically pure (2S,3S)- or (2R,3R)- 3-hydroxyleucine, see: (a) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181. (b) Caldwell, G. C.; Bondy, S. S. Synthesis 1990, 34. Also see: (c) Sunazuka, T.; Nagamitsu, T.; Tanaka, H.; Sprengeler, P. A.; Smith, A. B., III; Ōmura, S. Tetrahedron Lett. 1993, 34, 4447. (d) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (e) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799. (f) Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869. (g) Blaser, D.; Seebach, D. Liebigs Ann. Chem. 1991, 1067. (h) Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C.; Webber, T. Helv. Chim. Acta 1987, 70, 2037. (i) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39. (j) Reno, D. S.; Lotz, B. T.; Miller, M. J. Tetrahedron Lett. 1990, 31, 827. (k) Williams, R. M.; Im, M.-N.; Cao, J. J. Am. Chem. Soc. 1991, 113, 6976. (l) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. (m) Genet, J. P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. (n) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. (o) Suga, H.; Shi, X.; Ibata, T. J. Org. Chem. 1993, 58, 7397. (p) Horikawa, M. H.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
60. For the preparation of enantiomerically pure (2S,3S)- or (2R,3R)- 3-hydroxyleucine, see: (a) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181. (b) Caldwell, G. C.; Bondy, S. S. Synthesis 1990, 34. Also see: (c) Sunazuka, T.; Nagamitsu, T.; Tanaka, H.; Sprengeler, P. A.; Smith, A. B., III; Ōmura, S. Tetrahedron Lett. 1993, 34, 4447. (d) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (e) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799. (f) Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869. (g) Blaser, D.; Seebach, D. Liebigs Ann. Chem. 1991, 1067. (h) Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C.; Webber, T. Helv. Chim. Acta 1987, 70, 2037. (i) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39. (j) Reno, D. S.; Lotz, B. T.; Miller, M. J. Tetrahedron Lett. 1990, 31, 827. (k) Williams, R. M.; Im, M.-N.; Cao, J. J. Am. Chem. Soc. 1991, 113, 6976. (l) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. (m) Genet, J. P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. (n) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. (o) Suga, H.; Shi, X.; Ibata, T. J. Org. Chem. 1993, 58, 7397. (p) Horikawa, M. H.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
61. For the preparation of enantiomerically pure (2S,3S)- or (2R,3R)- 3-hydroxyleucine, see: (a) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181. (b) Caldwell, G. C.; Bondy, S. S. Synthesis 1990, 34. Also see: (c) Sunazuka, T.; Nagamitsu, T.; Tanaka, H.; Sprengeler, P. A.; Smith, A. B., III; Ōmura, S. Tetrahedron Lett. 1993, 34, 4447. (d) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (e) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799. (f) Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869. (g) Blaser, D.; Seebach, D. Liebigs Ann. Chem. 1991, 1067. (h) Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C.; Webber, T. Helv. Chim. Acta 1987, 70, 2037. (i) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39. (j) Reno, D. S.; Lotz, B. T.; Miller, M. J. Tetrahedron Lett. 1990, 31, 827. (k) Williams, R. M.; Im, M.-N.; Cao, J. J. Am. Chem. Soc. 1991, 113, 6976. (l) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. (m) Genet, J. P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. (n) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. (o) Suga, H.; Shi, X.; Ibata, T. J. Org. Chem. 1993, 58, 7397. (p) Horikawa, M. H.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
62. For the preparation of enantiomerically pure (2S,3S)- or (2R,3R)- 3-hydroxyleucine, see: (a) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181. (b) Caldwell, G. C.; Bondy, S. S. Synthesis 1990, 34. Also see: (c) Sunazuka, T.; Nagamitsu, T.; Tanaka, H.; Sprengeler, P. A.; Smith, A. B., III; Ōmura, S. Tetrahedron Lett. 1993, 34, 4447. (d) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (e) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799. (f) Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869. (g) Blaser, D.; Seebach, D. Liebigs Ann. Chem. 1991, 1067. (h) Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C.; Webber, T. Helv. Chim. Acta 1987, 70, 2037. (i) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39. (j) Reno, D. S.; Lotz, B. T.; Miller, M. J. Tetrahedron Lett. 1990, 31, 827. (k) Williams, R. M.; Im, M.-N.; Cao, J. J. Am. Chem. Soc. 1991, 113, 6976. (l) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. (m) Genet, J. P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. (n) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. (o) Suga, H.; Shi, X.; Ibata, T. J. Org. Chem. 1993, 58, 7397. (p) Horikawa, M. H.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
63. For the preparation of enantiomerically pure (2S,3S)- or (2R,3R)- 3-hydroxyleucine, see: (a) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181. (b) Caldwell, G. C.; Bondy, S. S. Synthesis 1990, 34. Also see: (c) Sunazuka, T.; Nagamitsu, T.; Tanaka, H.; Sprengeler, P. A.; Smith, A. B., III; Ōmura, S. Tetrahedron Lett. 1993, 34, 4447. (d) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (e) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799. (f) Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869. (g) Blaser, D.; Seebach, D. Liebigs Ann. Chem. 1991, 1067. (h) Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C.; Webber, T. Helv. Chim. Acta 1987, 70, 2037. (i) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39. (j) Reno, D. S.; Lotz, B. T.; Miller, M. J. Tetrahedron Lett. 1990, 31, 827. (k) Williams, R. M.; Im, M.-N.; Cao, J. J. Am. Chem. Soc. 1991, 113, 6976. (l) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. (m) Genet, J. P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. (n) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. (o) Suga, H.; Shi, X.; Ibata, T. J. Org. Chem. 1993, 58, 7397. (p) Horikawa, M. H.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
64. For the preparation of enantiomerically pure (2S,3S)- or (2R,3R)- 3-hydroxyleucine, see: (a) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181. (b) Caldwell, G. C.; Bondy, S. S. Synthesis 1990, 34. Also see: (c) Sunazuka, T.; Nagamitsu, T.; Tanaka, H.; Sprengeler, P. A.; Smith, A. B., III; Ōmura, S. Tetrahedron Lett. 1993, 34, 4447. (d) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (e) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799. (f) Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869. (g) Blaser, D.; Seebach, D. Liebigs Ann. Chem. 1991, 1067. (h) Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C.; Webber, T. Helv. Chim. Acta 1987, 70, 2037. (i) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39. (j) Reno, D. S.; Lotz, B. T.; Miller, M. J. Tetrahedron Lett. 1990, 31, 827. (k) Williams, R. M.; Im, M.-N.; Cao, J. J. Am. Chem. Soc. 1991, 113, 6976. (l) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. (m) Genet, J. P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. (n) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. (o) Suga, H.; Shi, X.; Ibata, T. J. Org. Chem. 1993, 58, 7397. (p) Horikawa, M. H.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
65. For the preparation of enantiomerically pure (2S,3S)- or (2R,3R)- 3-hydroxyleucine, see: (a) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181. (b) Caldwell, G. C.; Bondy, S. S. Synthesis 1990, 34. Also see: (c) Sunazuka, T.; Nagamitsu, T.; Tanaka, H.; Sprengeler, P. A.; Smith, A. B., III; Ōmura, S. Tetrahedron Lett. 1993, 34, 4447. (d) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (e) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799. (f) Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869. (g) Blaser, D.; Seebach, D. Liebigs Ann. Chem. 1991, 1067. (h) Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C.; Webber, T. Helv. Chim. Acta 1987, 70, 2037. (i) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39. (j) Reno, D. S.; Lotz, B. T.; Miller, M. J. Tetrahedron Lett. 1990, 31, 827. (k) Williams, R. M.; Im, M.-N.; Cao, J. J. Am. Chem. Soc. 1991, 113, 6976. (l) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. (m) Genet, J. P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. (n) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. (o) Suga, H.; Shi, X.; Ibata, T. J. Org. Chem. 1993, 58, 7397. (p) Horikawa, M. H.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
66. For the preparation of enantiomerically pure (2S,3S)- or (2R,3R)- 3-hydroxyleucine, see: (a) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181. (b) Caldwell, G. C.; Bondy, S. S. Synthesis 1990, 34. Also see: (c) Sunazuka, T.; Nagamitsu, T.; Tanaka, H.; Sprengeler, P. A.; Smith, A. B., III; Ōmura, S. Tetrahedron Lett. 1993, 34, 4447. (d) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (e) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799. (f) Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869. (g) Blaser, D.; Seebach, D. Liebigs Ann. Chem. 1991, 1067. (h) Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C.; Webber, T. Helv. Chim. Acta 1987, 70, 2037. (i) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39. (j) Reno, D. S.; Lotz, B. T.; Miller, M. J. Tetrahedron Lett. 1990, 31, 827. (k) Williams, R. M.; Im, M.-N.; Cao, J. J. Am. Chem. Soc. 1991, 113, 6976. (l) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. (m) Genet, J. P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. (n) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. (o) Suga, H.; Shi, X.; Ibata, T. J. Org. Chem. 1993, 58, 7397. (p) Horikawa, M. H.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
67. For the preparation of enantiomerically pure (2S,3S)- or (2R,3R)- 3-hydroxyleucine, see: (a) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181. (b) Caldwell, G. C.; Bondy, S. S. Synthesis 1990, 34. Also see: (c) Sunazuka, T.; Nagamitsu, T.; Tanaka, H.; Sprengeler, P. A.; Smith, A. B., III; Ōmura, S. Tetrahedron Lett. 1993, 34, 4447. (d) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637. (e) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799. (f) Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869. (g) Blaser, D.; Seebach, D. Liebigs Ann. Chem. 1991, 1067. (h) Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C.; Webber, T. Helv. Chim. Acta 1987, 70, 2037. (i) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39. (j) Reno, D. S.; Lotz, B. T.; Miller, M. J. Tetrahedron Lett. 1990, 31, 827. (k) Williams, R. M.; Im, M.-N.; Cao, J. J. Am. Chem. Soc. 1991, 113, 6976. (l) Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron 1988, 44, 5553. (m) Genet, J. P.; Juge, S.; Mallart, S. Tetrahedron Lett. 1988, 29, 6765. (n) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151. (o) Suga, H.; Shi, X.; Ibata, T. J. Org. Chem. 1993, 58, 7397. (p) Horikawa, M. H.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
68. (a) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-W.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768. For a review on catalytic asymmetric dihydroxylation and synthetic applications for 1,2-diols, see:
69. (b) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. Also see:
70. (c) Shao, H.; Goodman J. Org. Chem. 1996, 61, 2582.
71. Ahrgren, L.; Sutin, L. Org. Process Res. Dev. 1997, 1, 425.
72. The formation of such a dehydrohalogenated compound during a nucleophilic displacement by sodium azide has been reported before. See: Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151.
73. Pearlman, W. M. Tetrahedron Lett. 1967, 1663.
74. For a similar benzoyl group migration, see: Wang, Z.-M.; Kolb, H. C.; Sharpless, K. B. J. Org. Chem. 1994, 59, 5014.
75. An identical equilibration has been reported: Panek, J. S.; Masse, C. E. J. Org. Chem. 1998, 63, 2382-2384.
76. (a) Anh, N. T.; Einsenstein, O. Nouv. J. Chim. 1977, 1, 61.
77. (b) Anh, N. T. Topics in Current Chemistry; Springer-Verlag: New York, 1980; Vol. 88, p 145.
78. (a) Evans, D. A.; Ennis, M. E.; Le, T.; Mandel, N.; Mandel, G. J. Am. Chem. Soc. 1984, 106, 1154.
79. (b) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986, 27, 4961.
80. (c) Roush, W. R.; Palkowitz, A. D. J. Org. Chem. 1989, 54, 3009.
81. Fuji, H.; Taniguchi, M.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1992, 33, 4579.
82. Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327.
83. Gage, U. R.; Evans, D. A. Organic Syntheses; Wiley: New York, 1989; Collect. Vol. VIII, 339.
84. Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215.
85. Benzyl chloromethyl ether was prepared by a slight variation of the method described in the following: Coonor, D. S.; Klein, G. W.; Taylor, G. N. Org. Synth. 1972, 52, 16.
86. Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011.
87. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4156.
88. (b) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
89. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543
90. Ester 23 was prepared by benzylation of commercially available methyl (R)-(-)-3-hydroxy-2-methylpropionate. See: (a) Wessel, H.-P.; Iversen, T.; Bundle, D. R. J. Chem. Soc., Perkin Trans. I 1985, 2247. (b) Widmer, U. Synthesis 1987, 568.
91. Ester 23 was prepared by benzylation of commercially available methyl (R)-(-)-3-hydroxy-2-methylpropionate. See: (a) Wessel, H.-P.; Iversen, T.; Bundle, D. R. J. Chem. Soc., Perkin Trans. I 1985, 2247. (b) Widmer, U. Synthesis 1987, 568.
92. Lide, D. R. CRC Handbook of Chemistry and Physics, 78th ed.; CRC Press: New York, 1997-1998.
93. (a) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1998, 110, 1238.
94. (b) Lehmkuhl, H.; Kobs, H.-D. Liebigs Ann. Chem. 1968, 719, 11.
95. 1, a = 10.536(2) Å, b = 20.451(4) Å, c = 27.557(6) Å; α = β= γ = 90°, Z = 16, R1[I > 2σ(I)] = 0.0736.