Novel enantioselective approach to γ-lactams from chiral enol ethers: Synthesis of (-)-statine

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5210-5211

  Nebois, Pascal ^a   Greene, Andrew E ^a  

^a UNIV GRENOBLE ALPES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA LACTAM DERIVATIVE; STATINE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029766109     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961035d     Document Type: Article

References (30)

1. (a) Greene, A. E.; Charbonnier, F. Tetrahedron Lett. 1985, 26, 5525-5528.
2. (b) Greene, A. E.; Charbonnier, F.; Luche, M.-J.; Moyano, A. J. Am. Chem. Soc. 1987, 109, 4752-4753.
3. (c) B. M. de Azevedo, M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567-4569.
4. (d) Murta, M. M.; B. M. de Azevedo, M.; Greene, A. E. J. Org. Chem. 1993, 58, 7537-7541.
5. (e) B. M. de Azevedo; Greene, A. E. J. Org. Chem. 1995, 60, 4940-4942.
6. Significantly, it has been found that the cycloadducts (or a subsequent intermediate prior to removal of the chiral auxiliary) as a rule can be efficiently upgraded to diastereomeric purity by simple recrystallization.
7. For recent syntheses of chiral pyrrolidinones, see: (a) Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36-42. (b) Gennari, C.; Pain, G.; Moresca, D. J. Org. Chem. 1995, 60, 6248-6249. (c) Wei, Z.-Y.; Knaus, E. E. Tetrahedron Lett. 1993, 34, 4439-4442. (d) Wee, A. G. H.; Liu, B. Tetrahedron Lett. 1996, 37, 145-148 and references cited therein.
8. For recent syntheses of chiral pyrrolidinones, see: (a) Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36-42. (b) Gennari, C.; Pain, G.; Moresca, D. J. Org. Chem. 1995, 60, 6248-6249. (c) Wei, Z.-Y.; Knaus, E. E. Tetrahedron Lett. 1993, 34, 4439-4442. (d) Wee, A. G. H.; Liu, B. Tetrahedron Lett. 1996, 37, 145-148 and references cited therein.
9. For recent syntheses of chiral pyrrolidinones, see: (a) Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36-42. (b) Gennari, C.; Pain, G.; Moresca, D. J. Org. Chem. 1995, 60, 6248-6249. (c) Wei, Z.-Y.; Knaus, E. E. Tetrahedron Lett. 1993, 34, 4439-4442. (d) Wee, A. G. H.; Liu, B. Tetrahedron Lett. 1996, 37, 145-148 and references cited therein.
10. For recent syntheses of chiral pyrrolidinones, see: (a) Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36-42. (b) Gennari, C.; Pain, G.; Moresca, D. J. Org. Chem. 1995, 60, 6248-6249. (c) Wei, Z.-Y.; Knaus, E. E. Tetrahedron Lett. 1993, 34, 4439-4442. (d) Wee, A. G. H.; Liu, B. Tetrahedron Lett. 1996, 37, 145-148 and references cited therein.
11. For reviews on pyrrolidines, see: Attygalle, A. B.; Morgan, D. E. Chem. Soc. Rev. 1984, 13, 245-278. Massiot, G.; Delaude, C. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 27, Chapter 3. Numata, A.; Ibuka, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 31, Chapter 6. Pyrrolizidines, see: Robins, D. J. J. Nat. Prod. 1992, 9, 313-321. Indolizidines, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045-4066. Takahata, H.; Momose, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1993; Vol. 44, Chapter 3. Michael, J. P. J. Nat. Prod. 1995, 9, 535-552.
12. For reviews on pyrrolidines, see: Attygalle, A. B.; Morgan, D. E. Chem. Soc. Rev. 1984, 13, 245-278. Massiot, G.; Delaude, C. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 27, Chapter 3. Numata, A.; Ibuka, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 31, Chapter 6. Pyrrolizidines, see: Robins, D. J. J. Nat. Prod. 1992, 9, 313-321. Indolizidines, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045-4066. Takahata, H.; Momose, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1993; Vol. 44, Chapter 3. Michael, J. P. J. Nat. Prod. 1995, 9, 535-552.
13. For reviews on pyrrolidines, see: Attygalle, A. B.; Morgan, D. E. Chem. Soc. Rev. 1984, 13, 245-278. Massiot, G.; Delaude, C. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 27, Chapter 3. Numata, A.; Ibuka, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 31, Chapter 6. Pyrrolizidines, see: Robins, D. J. J. Nat. Prod. 1992, 9, 313-321. Indolizidines, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045-4066. Takahata, H.; Momose, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1993; Vol. 44, Chapter 3. Michael, J. P. J. Nat. Prod. 1995, 9, 535-552.
14. For reviews on pyrrolidines, see: Attygalle, A. B.; Morgan, D. E. Chem. Soc. Rev. 1984, 13, 245-278. Massiot, G.; Delaude, C. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 27, Chapter 3. Numata, A.; Ibuka, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 31, Chapter 6. Pyrrolizidines, see: Robins, D. J. J. Nat. Prod. 1992, 9, 313-321. Indolizidines, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045-4066. Takahata, H.; Momose, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1993; Vol. 44, Chapter 3. Michael, J. P. J. Nat. Prod. 1995, 9, 535-552.
15. For reviews on pyrrolidines, see: Attygalle, A. B.; Morgan, D. E. Chem. Soc. Rev. 1984, 13, 245-278. Massiot, G.; Delaude, C. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 27, Chapter 3. Numata, A.; Ibuka, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 31, Chapter 6. Pyrrolizidines, see: Robins, D. J. J. Nat. Prod. 1992, 9, 313-321. Indolizidines, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045-4066. Takahata, H.; Momose, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1993; Vol. 44, Chapter 3. Michael, J. P. J. Nat. Prod. 1995, 9, 535-552.
16. For reviews on pyrrolidines, see: Attygalle, A. B.; Morgan, D. E. Chem. Soc. Rev. 1984, 13, 245-278. Massiot, G.; Delaude, C. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 27, Chapter 3. Numata, A.; Ibuka, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 31, Chapter 6. Pyrrolizidines, see: Robins, D. J. J. Nat. Prod. 1992, 9, 313-321. Indolizidines, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045-4066. Takahata, H.; Momose, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1993; Vol. 44, Chapter 3. Michael, J. P. J. Nat. Prod. 1995, 9, 535-552.
17. For reviews on pyrrolidines, see: Attygalle, A. B.; Morgan, D. E. Chem. Soc. Rev. 1984, 13, 245-278. Massiot, G.; Delaude, C. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 27, Chapter 3. Numata, A.; Ibuka, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 31, Chapter 6. Pyrrolizidines, see: Robins, D. J. J. Nat. Prod. 1992, 9, 313-321. Indolizidines, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045-4066. Takahata, H.; Momose, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1993; Vol. 44, Chapter 3. Michael, J. P. J. Nat. Prod. 1995, 9, 535-552.
18. D +46.2 (c 1, chloroform); mp 84-85 °C. (The values cited in ref 1e are in error.)
19. (a) Moyano, A.; Charbonnier, F.; Greene, A. E. J. Org. Chem. 1987, 52, 2919-2922.
20. (b) Kann, N.; Bernardes, V.; Greene, A. E. Org. Synth., in press.
21. Salomon, M. F.; Salomon, R. G.; Gleim, R. D. J. Org. Chem. 1976, 41, 3983-3987.
22. 2: C, 77.47; H, 10.66; N, 3.61. Found: C, 77.80; H, 10.67; N, 3.48.
23. For a recent review on ketene cycloaddition chemistry, see: Hyatt, J. A.; Raynolds, P. W. Org. React. 1994, 45, 159-646.
24. Tamura, Y.; Minamikawa, J.; Ikeda, M. Synthesis 1977, 1-17. See also: Luh, T.-Y.; Chow, H.-F.; Leung, W. Y.; Tam, S. W. Tetrahedron 1985, 41, 519-525.
25. Tamura, Y.; Minamikawa, J.; Ikeda, M. Synthesis 1977, 1-17. See also: Luh, T.-Y.; Chow, H.-F.; Leung, W. Y.; Tam, S. W. Tetrahedron 1985, 41, 519-525.
26. Johnston, B. D.; Slessor, K. N.; Oehlschlager, A. C. J. Org. Chem. 1985, 50, 114-117.
27. With menthol as the chiral auxiliary, similar results were obtained.
28. For syntheses of statine and leading references concerning its potential use, see: (a) Rich, D. H.; Sun, E. T.; Boparai, A. S. J. Org. Chem. 1978, 43, 3624-3626. (b) Rittle, K. E.; Homnick, C. F.; Ponticello, G. S.; Evans, B. E. J. Org. Chem. 1982, 47, 3016-3018. (c) Woo, P. W. K. Tetrahedron Lett. 1985, 26, 2973-2976. See also ref 3b and references cited therein.
29. For syntheses of statine and leading references concerning its potential use, see: (a) Rich, D. H.; Sun, E. T.; Boparai, A. S. J. Org. Chem. 1978, 43, 3624-3626. (b) Rittle, K. E.; Homnick, C. F.; Ponticello, G. S.; Evans, B. E. J. Org. Chem. 1982, 47, 3016-3018. (c) Woo, P. W. K. Tetrahedron Lett. 1985, 26, 2973-2976. See also ref 3b and references cited therein.
30. For syntheses of statine and leading references concerning its potential use, see: (a) Rich, D. H.; Sun, E. T.; Boparai, A. S. J. Org. Chem. 1978, 43, 3624-3626. (b) Rittle, K. E.; Homnick, C. F.; Ponticello, G. S.; Evans, B. E. J. Org. Chem. 1982, 47, 3016-3018. (c) Woo, P. W. K. Tetrahedron Lett. 1985, 26, 2973-2976. See also ref 3b and references cited therein.