Formal total syntheses of the β-lactam antibiotics thienamycin and PS-5

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2413-2427

  Jacobi, Peter A ^a   Murphree, Shaun ^a   Rupprecht, Frederic ^a   Zheng, Wanjun ^a  

^a WESLEYAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 (2 ACETAMIDOETHYL)THIO 6 ETHYL 7 OXO 1 AZABICYCLO[3.2.0]HEPT 2 ENE 2 CARBOXYLIC ACID; BETA LACTAM ANTIBIOTIC; THIENAMYCIN;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029928601     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952092u     Document Type: Article

References (96)

1. (a) Kahan, J. S.; Kahan, F. M.; Stapley, E. O.; Goegelman, R. T.; Hernandez, S. U.S. Patent 3950357, 1976; Chem. Abstr. 1976, 85, 92190t. See also: Kahan, J. S.; Kahan, F.; Goegelman, R.; Currie, S. A.; Jackson, M.; Stapely, E. O.; Miller, T. W.; Miller, A. K.; Hendlin, D.; Mochales, S.; Hernandez, S.; Woodruff, H. B.; Birnbaum, J. J. Antibiot. 1979, 32, 1.
2. (a) Kahan, J. S.; Kahan, F. M.; Stapley, E. O.; Goegelman, R. T.; Hernandez, S. U.S. Patent 3950357, 1976; Chem. Abstr. 1976, 85, 92190t. See also: Kahan, J. S.; Kahan, F.; Goegelman, R.; Currie, S. A.; Jackson, M.; Stapely, E. O.; Miller, T. W.; Miller, A. K.; Hendlin, D.; Mochales, S.; Hernandez, S.; Woodruff, H. B.; Birnbaum, J. J. Antibiot. 1979, 32, 1.
3. (b) Albers-Schonberg, G.; Arison, B. H.; Hensens, O. D.; Hirshfield, J.; Hoogsteen, K.; Kaczka, E. A.; Rhoads, R. E.; Kahan, J. S.; Kahan, F. M.; Ratcliffe, R. W.; Walton, E.; Ruswinkle, L. J.; Morin, R. B.; Christensen, B. G. J. Am. Chem. Soc. 1978, 100, 6491.
4. (c) Leanza, W. J.; Wildonger, K. J.; Miller, T. W.; Christensen, B. G. J. Med. Chem. 1979, 22, 1435.
5. (a) Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796.
6. For references to earlv syntheses of PS-5 (4), see: (b) Wasserman, H. H.; Han, W. T. Tetrahedron Lett. 1984, 25, 3747 (cf. also ref 12i and references cited therein).
7. Corbett, D. F.; Coulton, S.; Southgate, R. J. Chem. Soc., Perkin Trans. 1 1982, 3011 and references cited therein.
8. (a) Shih, D. H.; Baker, F.; Cama, L.; Christensen, B. G. Heterocycles 1984, 21, 29.
9. (b) Hatanaka, M. Tetrahedron Lett. 1987, 28, 83.
10. (c) Udodong, U. E.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 2103.
11. (d) Kawabata, T.; Kimura, Y.; Ito, Y.; Terashima, S.; Sasaki, A.; Sunagawa, M. Tetrahedron 1988, 44, 2149 and references cited therein. Kaga, H.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 113.
12. (d) Kawabata, T.; Kimura, Y.; Ito, Y.; Terashima, S.; Sasaki, A.; Sunagawa, M. Tetrahedron 1988, 44, 2149 and references cited therein. Kaga, H.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 113.
13. (e) Rama Rao, A. V.; Gurjar, M. K.; Khare, V. B.; Ashok, B.; Deshmukh, M. N. Tetrahedron Lett. 1990, 31, 271.
14. (a) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498.
15. (b) Melillo, D. G.; Shinkai, L; Liu, T.; Ryan, K.; Sletzinger, M. Tetrahedron Lett. 1980, 21, 2783.
16. (c) Melillo, D. G.; Liu, T.; Ryan, K.; Sletzinger, M.; Shinkai, I. Tetrahedron Lett. 1981, 22, 913.
17. (d) Liu, T. M. H.; Melillo, D. G.; Ryan, K. M.; Shinkai, I.; Setzinger, M. U.S. Patent 4,349,687, 1982, Merck & Co.
18. (a) Karady, S.; Amato, J. S.; Reamer, R. A.; Weinstock, L. M. J. Am. Chem. Soc. 1981, 103, 6765.
19. (b) Barrett, A. G. M.; Quayle, P. J. Chem. Soc., Chem. Commun. 1981, 1076.
20. (c) Greengrass, C. W.; Nobbs, M. S. Tetrahedron Lett. 1981, 22, 5339.
21. (d) Greengrass, C. W.; Hoople, D. W. T. Tetrahedron Lett. 1981, 22, 5335.
22. (e) Reider, P. J.; Rayford, R.; Grabowski, E. J. Tetrahedron Lett. 1982, 23, 379.
23. (f) Koller, W.; Linkies, A.; Pietsch, H.; Rehling, H.; Reuschling, D. Tetrahedron Lett. 1982, 23, 1545.
24. (g) Reider, P. J.; Grabowski, E. J. J. Tetrahedron Lett. 1982, 23, 2293.
25. (h) Aratani, M.; Sawada, K.; Hashimoto, M. Tetrahedron Lett. 1982, 23, 3921.
26. (i) Kraus, G. A.; Neuenschwander, K. J. Chem. Soc., Chem. Commun. 1982, 134.
27. (j) Kametani, T.; Kanaya, N.; Mochizuki, T.; Honda, T. Heterocycles 1982, 19, 1023.
28. (k) Fujimoto, K.; Iwano, Y.; Hirai, K. Tetrahedron Lett. 1985, 26, 89.
29. (l) Hua, D. H.; Verma, A. Tetrahedron Lett. 1985, 26, 547.
30. (m) Tijima, Y.; Yoshida, A.; Takeda, N.; Oida, S. Tetrahedron Lett. 1985, 26, 637.
31. (n) Chiba, T.; Nagatsuma, M.; Nakai, T. Chem. Lett. 1985, 1343.
32. (o) Fliri, H.; Mak, C.-P. J. Org. Chem. 1985, 50, 3438.
33. (p) Meyers, A. I.; Sowin, T. J.; Scholz, S.; Ueda, Y. Tetrahedron Lett. 1987, 28, 5103.
34. (q) Sowin, T. J.; Meyers, A. I. J. Org. Chem. 1988, 53, 4154.
35. (a) Ha, D.-C.; Hart, D. J.; Yang, T.-K. J. Am. Chem. Soc. 1984, 106, 4819.
36. (b) Shibasaki, M.; Iimori, T. Tetrahedron Lett. 1985, 26, 1523.
37. (c) Cainelli, G.; Contento, M.; Giacomini, D.; Panunzio, M. Tetrahedron Lett. 1985, 26, 937.
38. (d) Hatakana, M.; Nitta, H. Tetrahedron Lett. 1987, 28, 69.
39. (e) Yamada, T.; Suzuki, H.; Mukaiyama, T. Chem. Lett. 1987, 293.
40. (f) Gennari, C.; Venlurini, S.; Gislon, G.; Schimperna, G. Tetrahedron Lett. 1987, 28, 227.
41. (g) Kunz, H.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1989, 28, 1068.
42. (h) Corey, E. J.; Decicco, C. P.; Newbold, C. N. Tetrahedron Lett. 1991, 32, 5287.
43. (a) d'Angelo, J.; Maddaluno, J. J. Am. Chem. Soc. 1986, 108, 8112.
44. (b) Estermann, H.; Seebach, D. Helv. Chim. Acta 1988, 71, 1824.
45. (c) Davies, S. G.; Ichihara, O. Tetrahedron Asymmetry 1991, 2, 183.
46. (a) Kametani, T.; Chu, S.-D.; Honda, T. J. Chem. Soc., Perkin Trans. 1 1988, 1593.
47. (b) Ihara, M.; Takahashi, M.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Perkin Trans. 1 1989, 2215.
48. (a) Lubell, W. D.; Kitamura, M.; Noyori, R. Tetrahedron Asymmetry 1991, 2, 543.
49. (b) Potin, D.; Dumas, P.; d'Angelo, J. J. Am. Chem. Soc. 1990, 112, 3483.
50. (a) Andres, C.; Gonzalez, A.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron Lett. 1992, 33, 2895 and references cited therein.
51. (b) Juaristi, E.; Quintana, D. Tetrahedron Lett. 1992, 33, 723 and references cited therein.
52. (c) Amoroso, R.; Cardillo, G.; Tomasini, C. Tetrahedron Lett. 1992, 33, 2725 and references cited therein.
53. For recent reviews on the synthesis of thienamycin (1) and related materials, see: (a) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A-ur, Ed.; Elsevier Science: Amsterdam, 1989; Vol. 4. (c) Bateson, J. H. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1991; Vol. 3. See also: (d) Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098 and references cited therein. (e) Grieco, P. A.; Flynn, D. L.; Zelle, R. E. J. Am. Chem. Soc. 1984, 106, 6414. (f) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498. (g) Evans, D. A.; Sjogren, E. B Tetrahedron Lett. 1986, 27, 4961. (h) Corbett, D. F.; Coulton, S.; Southgate, R J. Chem. Soc., Perkin Trans. 1 1982, 3011 and references cited therein. (i) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986, 27, 3119. (j) Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796. (k) Shono, T.; Kise, N.; Sanda, F.; Ohi, S.; Yoshioka K. Tetrahedron Lett. 1989, 30, 1253. (l) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498 and references cited therein. (m) Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807. (n) Georg, G. I.; Akgun, E. Tetrahedron Lett. 1990, 31, 3267. (o) Chackahamannil, S.; Fett, N.; Kirkup, M.; Afonso, A.; Ganguly, A. K. J. Org. Chem. 1988, 53, 450. (p) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161. For an alternative synthesis of β-lactams involving intramolecular alkylation, see: (q) Wasserman, H. H.; Hlasta, D. J. Tetrahedron Lett. 1979, 20, 549.
54. For recent reviews on the synthesis of thienamycin (1) and related materials, see: (a) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A-ur, Ed.; Elsevier Science: Amsterdam, 1989; Vol. 4. (c) Bateson, J. H. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1991; Vol. 3. See also: (d) Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098 and references cited therein. (e) Grieco, P. A.; Flynn, D. L.; Zelle, R. E. J. Am. Chem. Soc. 1984, 106, 6414. (f) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498. (g) Evans, D. A.; Sjogren, E. B Tetrahedron Lett. 1986, 27, 4961. (h) Corbett, D. F.; Coulton, S.; Southgate, R J. Chem. Soc., Perkin Trans. 1 1982, 3011 and references cited therein. (i) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986, 27, 3119. (j) Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796. (k) Shono, T.; Kise, N.; Sanda, F.; Ohi, S.; Yoshioka K. Tetrahedron Lett. 1989, 30, 1253. (l) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498 and references cited therein. (m) Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807. (n) Georg, G. I.; Akgun, E. Tetrahedron Lett. 1990, 31, 3267. (o) Chackahamannil, S.; Fett, N.; Kirkup, M.; Afonso, A.; Ganguly, A. K. J. Org. Chem. 1988, 53, 450. (p) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161. For an alternative synthesis of β-lactams involving intramolecular alkylation, see: (q) Wasserman, H. H.; Hlasta, D. J. Tetrahedron Lett. 1979, 20, 549.
55. For recent reviews on the synthesis of thienamycin (1) and related materials, see: (a) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A-ur, Ed.; Elsevier Science: Amsterdam, 1989; Vol. 4. (c) Bateson, J. H. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1991; Vol. 3. See also: (d) Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098 and references cited therein. (e) Grieco, P. A.; Flynn, D. L.; Zelle, R. E. J. Am. Chem. Soc. 1984, 106, 6414. (f) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498. (g) Evans, D. A.; Sjogren, E. B Tetrahedron Lett. 1986, 27, 4961. (h) Corbett, D. F.; Coulton, S.; Southgate, R J. Chem. Soc., Perkin Trans. 1 1982, 3011 and references cited therein. (i) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986, 27, 3119. (j) Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796. (k) Shono, T.; Kise, N.; Sanda, F.; Ohi, S.; Yoshioka K. Tetrahedron Lett. 1989, 30, 1253. (l) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498 and references cited therein. (m) Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807. (n) Georg, G. I.; Akgun, E. Tetrahedron Lett. 1990, 31, 3267. (o) Chackahamannil, S.; Fett, N.; Kirkup, M.; Afonso, A.; Ganguly, A. K. J. Org. Chem. 1988, 53, 450. (p) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161. For an alternative synthesis of β-lactams involving intramolecular alkylation, see: (q) Wasserman, H. H.; Hlasta, D. J. Tetrahedron Lett. 1979, 20, 549.
56. For recent reviews on the synthesis of thienamycin (1) and related materials, see: (a) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A-ur, Ed.; Elsevier Science: Amsterdam, 1989; Vol. 4. (c) Bateson, J. H. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1991; Vol. 3. See also: (d) Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098 and references cited therein. (e) Grieco, P. A.; Flynn, D. L.; Zelle, R. E. J. Am. Chem. Soc. 1984, 106, 6414. (f) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498. (g) Evans, D. A.; Sjogren, E. B Tetrahedron Lett. 1986, 27, 4961. (h) Corbett, D. F.; Coulton, S.; Southgate, R J. Chem. Soc., Perkin Trans. 1 1982, 3011 and references cited therein. (i) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986, 27, 3119. (j) Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796. (k) Shono, T.; Kise, N.; Sanda, F.; Ohi, S.; Yoshioka K. Tetrahedron Lett. 1989, 30, 1253. (l) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498 and references cited therein. (m) Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807. (n) Georg, G. I.; Akgun, E. Tetrahedron Lett. 1990, 31, 3267. (o) Chackahamannil, S.; Fett, N.; Kirkup, M.; Afonso, A.; Ganguly, A. K. J. Org. Chem. 1988, 53, 450. (p) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161. For an alternative synthesis of β-lactams involving intramolecular alkylation, see: (q) Wasserman, H. H.; Hlasta, D. J. Tetrahedron Lett. 1979, 20, 549.
57. For recent reviews on the synthesis of thienamycin (1) and related materials, see: (a) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A-ur, Ed.; Elsevier Science: Amsterdam, 1989; Vol. 4. (c) Bateson, J. H. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1991; Vol. 3. See also: (d) Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098 and references cited therein. (e) Grieco, P. A.; Flynn, D. L.; Zelle, R. E. J. Am. Chem. Soc. 1984, 106, 6414. (f) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498. (g) Evans, D. A.; Sjogren, E. B Tetrahedron Lett. 1986, 27, 4961. (h) Corbett, D. F.; Coulton, S.; Southgate, R J. Chem. Soc., Perkin Trans. 1 1982, 3011 and references cited therein. (i) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986, 27, 3119. (j) Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796. (k) Shono, T.; Kise, N.; Sanda, F.; Ohi, S.; Yoshioka K. Tetrahedron Lett. 1989, 30, 1253. (l) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498 and references cited therein. (m) Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807. (n) Georg, G. I.; Akgun, E. Tetrahedron Lett. 1990, 31, 3267. (o) Chackahamannil, S.; Fett, N.; Kirkup, M.; Afonso, A.; Ganguly, A. K. J. Org. Chem. 1988, 53, 450. (p) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161. For an alternative synthesis of β-lactams involving intramolecular alkylation, see: (q) Wasserman, H. H.; Hlasta, D. J. Tetrahedron Lett. 1979, 20, 549.
58. For recent reviews on the synthesis of thienamycin (1) and related materials, see: (a) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A-ur, Ed.; Elsevier Science: Amsterdam, 1989; Vol. 4. (c) Bateson, J. H. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1991; Vol. 3. See also: (d) Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098 and references cited therein. (e) Grieco, P. A.; Flynn, D. L.; Zelle, R. E. J. Am. Chem. Soc. 1984, 106, 6414. (f) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498. (g) Evans, D. A.; Sjogren, E. B Tetrahedron Lett. 1986, 27, 4961. (h) Corbett, D. F.; Coulton, S.; Southgate, R J. Chem. Soc., Perkin Trans. 1 1982, 3011 and references cited therein. (i) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986, 27, 3119. (j) Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796. (k) Shono, T.; Kise, N.; Sanda, F.; Ohi, S.; Yoshioka K. Tetrahedron Lett. 1989, 30, 1253. (l) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498 and references cited therein. (m) Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807. (n) Georg, G. I.; Akgun, E. Tetrahedron Lett. 1990, 31, 3267. (o) Chackahamannil, S.; Fett, N.; Kirkup, M.; Afonso, A.; Ganguly, A. K. J. Org. Chem. 1988, 53, 450. (p) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161. For an alternative synthesis of β-lactams involving intramolecular alkylation, see: (q) Wasserman, H. H.; Hlasta, D. J. Tetrahedron Lett. 1979, 20, 549.
59. For recent reviews on the synthesis of thienamycin (1) and related materials, see: (a) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A-ur, Ed.; Elsevier Science: Amsterdam, 1989; Vol. 4. (c) Bateson, J. H. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1991; Vol. 3. See also: (d) Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098 and references cited therein. (e) Grieco, P. A.; Flynn, D. L.; Zelle, R. E. J. Am. Chem. Soc. 1984, 106, 6414. (f) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498. (g) Evans, D. A.; Sjogren, E. B Tetrahedron Lett. 1986, 27, 4961. (h) Corbett, D. F.; Coulton, S.; Southgate, R J. Chem. Soc., Perkin Trans. 1 1982, 3011 and references cited therein. (i) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986, 27, 3119. (j) Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796. (k) Shono, T.; Kise, N.; Sanda, F.; Ohi, S.; Yoshioka K. Tetrahedron Lett. 1989, 30, 1253. (l) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498 and references cited therein. (m) Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807. (n) Georg, G. I.; Akgun, E. Tetrahedron Lett. 1990, 31, 3267. (o) Chackahamannil, S.; Fett, N.; Kirkup, M.; Afonso, A.; Ganguly, A. K. J. Org. Chem. 1988, 53, 450. (p) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161. For an alternative synthesis of β-lactams involving intramolecular alkylation, see: (q) Wasserman, H. H.; Hlasta, D. J. Tetrahedron Lett. 1979, 20, 549.
60. For recent reviews on the synthesis of thienamycin (1) and related materials, see: (a) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A-ur, Ed.; Elsevier Science: Amsterdam, 1989; Vol. 4. (c) Bateson, J. H. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1991; Vol. 3. See also: (d) Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098 and references cited therein. (e) Grieco, P. A.; Flynn, D. L.; Zelle, R. E. J. Am. Chem. Soc. 1984, 106, 6414. (f) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498. (g) Evans, D. A.; Sjogren, E. B Tetrahedron Lett. 1986, 27, 4961. (h) Corbett, D. F.; Coulton, S.; Southgate, R J. Chem. Soc., Perkin Trans. 1 1982, 3011 and references cited therein. (i) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986, 27, 3119. (j) Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796. (k) Shono, T.; Kise, N.; Sanda, F.; Ohi, S.; Yoshioka K. Tetrahedron Lett. 1989, 30, 1253. (l) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498 and references cited therein. (m) Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807. (n) Georg, G. I.; Akgun, E. Tetrahedron Lett. 1990, 31, 3267. (o) Chackahamannil, S.; Fett, N.; Kirkup, M.; Afonso, A.; Ganguly, A. K. J. Org. Chem. 1988, 53, 450. (p) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161. For an alternative synthesis of β-lactams involving intramolecular alkylation, see: (q) Wasserman, H. H.; Hlasta, D. J. Tetrahedron Lett. 1979, 20, 549.
61. For recent reviews on the synthesis of thienamycin (1) and related materials, see: (a) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A-ur, Ed.; Elsevier Science: Amsterdam, 1989; Vol. 4. (c) Bateson, J. H. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1991; Vol. 3. See also: (d) Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098 and references cited therein. (e) Grieco, P. A.; Flynn, D. L.; Zelle, R. E. J. Am. Chem. Soc. 1984, 106, 6414. (f) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498. (g) Evans, D. A.; Sjogren, E. B Tetrahedron Lett. 1986, 27, 4961. (h) Corbett, D. F.; Coulton, S.; Southgate, R J. Chem. Soc., Perkin Trans. 1 1982, 3011 and references cited therein. (i) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986, 27, 3119. (j) Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796. (k) Shono, T.; Kise, N.; Sanda, F.; Ohi, S.; Yoshioka K. Tetrahedron Lett. 1989, 30, 1253. (l) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498 and references cited therein. (m) Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807. (n) Georg, G. I.; Akgun, E. Tetrahedron Lett. 1990, 31, 3267. (o) Chackahamannil, S.; Fett, N.; Kirkup, M.; Afonso, A.; Ganguly, A. K. J. Org. Chem. 1988, 53, 450. (p) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161. For an alternative synthesis of β-lactams involving intramolecular alkylation, see: (q) Wasserman, H. H.; Hlasta, D. J. Tetrahedron Lett. 1979, 20, 549.
62. For recent reviews on the synthesis of thienamycin (1) and related materials, see: (a) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A-ur, Ed.; Elsevier Science: Amsterdam, 1989; Vol. 4. (c) Bateson, J. H. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1991; Vol. 3. See also: (d) Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098 and references cited therein. (e) Grieco, P. A.; Flynn, D. L.; Zelle, R. E. J. Am. Chem. Soc. 1984, 106, 6414. (f) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498. (g) Evans, D. A.; Sjogren, E. B Tetrahedron Lett. 1986, 27, 4961. (h) Corbett, D. F.; Coulton, S.; Southgate, R J. Chem. Soc., Perkin Trans. 1 1982, 3011 and references cited therein. (i) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986, 27, 3119. (j) Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796. (k) Shono, T.; Kise, N.; Sanda, F.; Ohi, S.; Yoshioka K. Tetrahedron Lett. 1989, 30, 1253. (l) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498 and references cited therein. (m) Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807. (n) Georg, G. I.; Akgun, E. Tetrahedron Lett. 1990, 31, 3267. (o) Chackahamannil, S.; Fett, N.; Kirkup, M.; Afonso, A.; Ganguly, A. K. J. Org. Chem. 1988, 53, 450. (p) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161. For an alternative synthesis of β-lactams involving intramolecular alkylation, see: (q) Wasserman, H. H.; Hlasta, D. J. Tetrahedron Lett. 1979, 20, 549.
63. For recent reviews on the synthesis of thienamycin (1) and related materials, see: (a) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A-ur, Ed.; Elsevier Science: Amsterdam, 1989; Vol. 4. (c) Bateson, J. H. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1991; Vol. 3. See also: (d) Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098 and references cited therein. (e) Grieco, P. A.; Flynn, D. L.; Zelle, R. E. J. Am. Chem. Soc. 1984, 106, 6414. (f) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498. (g) Evans, D. A.; Sjogren, E. B Tetrahedron Lett. 1986, 27, 4961. (h) Corbett, D. F.; Coulton, S.; Southgate, R J. Chem. Soc., Perkin Trans. 1 1982, 3011 and references cited therein. (i) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986, 27, 3119. (j) Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796. (k) Shono, T.; Kise, N.; Sanda, F.; Ohi, S.; Yoshioka K. Tetrahedron Lett. 1989, 30, 1253. (l) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498 and references cited therein. (m) Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807. (n) Georg, G. I.; Akgun, E. Tetrahedron Lett. 1990, 31, 3267. (o) Chackahamannil, S.; Fett, N.; Kirkup, M.; Afonso, A.; Ganguly, A. K. J. Org. Chem. 1988, 53, 450. (p) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161. For an alternative synthesis of β-lactams involving intramolecular alkylation, see: (q) Wasserman, H. H.; Hlasta, D. J. Tetrahedron Lett. 1979, 20, 549.
64. For recent reviews on the synthesis of thienamycin (1) and related materials, see: (a) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A-ur, Ed.; Elsevier Science: Amsterdam, 1989; Vol. 4. (c) Bateson, J. H. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1991; Vol. 3. See also: (d) Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098 and references cited therein. (e) Grieco, P. A.; Flynn, D. L.; Zelle, R. E. J. Am. Chem. Soc. 1984, 106, 6414. (f) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498. (g) Evans, D. A.; Sjogren, E. B Tetrahedron Lett. 1986, 27, 4961. (h) Corbett, D. F.; Coulton, S.; Southgate, R J. Chem. Soc., Perkin Trans. 1 1982, 3011 and references cited therein. (i) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986, 27, 3119. (j) Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796. (k) Shono, T.; Kise, N.; Sanda, F.; Ohi, S.; Yoshioka K. Tetrahedron Lett. 1989, 30, 1253. (l) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498 and references cited therein. (m) Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807. (n) Georg, G. I.; Akgun, E. Tetrahedron Lett. 1990, 31, 3267. (o) Chackahamannil, S.; Fett, N.; Kirkup, M.; Afonso, A.; Ganguly, A. K. J. Org. Chem. 1988, 53, 450. (p) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161. For an alternative synthesis of β-lactams involving intramolecular alkylation, see: (q) Wasserman, H. H.; Hlasta, D. J. Tetrahedron Lett. 1979, 20, 549.
65. For recent reviews on the synthesis of thienamycin (1) and related materials, see: (a) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A-ur, Ed.; Elsevier Science: Amsterdam, 1989; Vol. 4. (c) Bateson, J. H. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1991; Vol. 3. See also: (d) Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098 and references cited therein. (e) Grieco, P. A.; Flynn, D. L.; Zelle, R. E. J. Am. Chem. Soc. 1984, 106, 6414. (f) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498. (g) Evans, D. A.; Sjogren, E. B Tetrahedron Lett. 1986, 27, 4961. (h) Corbett, D. F.; Coulton, S.; Southgate, R J. Chem. Soc., Perkin Trans. 1 1982, 3011 and references cited therein. (i) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986, 27, 3119. (j) Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796. (k) Shono, T.; Kise, N.; Sanda, F.; Ohi, S.; Yoshioka K. Tetrahedron Lett. 1989, 30, 1253. (l) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498 and references cited therein. (m) Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807. (n) Georg, G. I.; Akgun, E. Tetrahedron Lett. 1990, 31, 3267. (o) Chackahamannil, S.; Fett, N.; Kirkup, M.; Afonso, A.; Ganguly, A. K. J. Org. Chem. 1988, 53, 450. (p) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161. For an alternative synthesis of β-lactams involving intramolecular alkylation, see: (q) Wasserman, H. H.; Hlasta, D. J. Tetrahedron Lett. 1979, 20, 549.
66. For recent reviews on the synthesis of thienamycin (1) and related materials, see: (a) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A-ur, Ed.; Elsevier Science: Amsterdam, 1989; Vol. 4. (c) Bateson, J. H. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1991; Vol. 3. See also: (d) Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098 and references cited therein. (e) Grieco, P. A.; Flynn, D. L.; Zelle, R. E. J. Am. Chem. Soc. 1984, 106, 6414. (f) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498. (g) Evans, D. A.; Sjogren, E. B Tetrahedron Lett. 1986, 27, 4961. (h) Corbett, D. F.; Coulton, S.; Southgate, R J. Chem. Soc., Perkin Trans. 1 1982, 3011 and references cited therein. (i) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986, 27, 3119. (j) Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796. (k) Shono, T.; Kise, N.; Sanda, F.; Ohi, S.; Yoshioka K. Tetrahedron Lett. 1989, 30, 1253. (l) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498 and references cited therein. (m) Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807. (n) Georg, G. I.; Akgun, E. Tetrahedron Lett. 1990, 31, 3267. (o) Chackahamannil, S.; Fett, N.; Kirkup, M.; Afonso, A.; Ganguly, A. K. J. Org. Chem. 1988, 53, 450. (p) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161. For an alternative synthesis of β-lactams involving intramolecular alkylation, see: (q) Wasserman, H. H.; Hlasta, D. J. Tetrahedron Lett. 1979, 20, 549.
67. For recent reviews on the synthesis of thienamycin (1) and related materials, see: (a) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A-ur, Ed.; Elsevier Science: Amsterdam, 1989; Vol. 4. (c) Bateson, J. H. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1991; Vol. 3. See also: (d) Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098 and references cited therein. (e) Grieco, P. A.; Flynn, D. L.; Zelle, R. E. J. Am. Chem. Soc. 1984, 106, 6414. (f) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498. (g) Evans, D. A.; Sjogren, E. B Tetrahedron Lett. 1986, 27, 4961. (h) Corbett, D. F.; Coulton, S.; Southgate, R J. Chem. Soc., Perkin Trans. 1 1982, 3011 and references cited therein. (i) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986, 27, 3119. (j) Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796. (k) Shono, T.; Kise, N.; Sanda, F.; Ohi, S.; Yoshioka K. Tetrahedron Lett. 1989, 30, 1253. (l) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498 and references cited therein. (m) Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807. (n) Georg, G. I.; Akgun, E. Tetrahedron Lett. 1990, 31, 3267. (o) Chackahamannil, S.; Fett, N.; Kirkup, M.; Afonso, A.; Ganguly, A. K. J. Org. Chem. 1988, 53, 450. (p) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161. For an alternative synthesis of β-lactams involving intramolecular alkylation, see: (q) Wasserman, H. H.; Hlasta, D. J. Tetrahedron Lett. 1979, 20, 549.
68. For recent reviews on the synthesis of thienamycin (1) and related materials, see: (a) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A-ur, Ed.; Elsevier Science: Amsterdam, 1989; Vol. 4. (c) Bateson, J. H. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1991; Vol. 3. See also: (d) Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098 and references cited therein. (e) Grieco, P. A.; Flynn, D. L.; Zelle, R. E. J. Am. Chem. Soc. 1984, 106, 6414. (f) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498. (g) Evans, D. A.; Sjogren, E. B Tetrahedron Lett. 1986, 27, 4961. (h) Corbett, D. F.; Coulton, S.; Southgate, R J. Chem. Soc., Perkin Trans. 1 1982, 3011 and references cited therein. (i) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986, 27, 3119. (j) Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796. (k) Shono, T.; Kise, N.; Sanda, F.; Ohi, S.; Yoshioka K. Tetrahedron Lett. 1989, 30, 1253. (l) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498 and references cited therein. (m) Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807. (n) Georg, G. I.; Akgun, E. Tetrahedron Lett. 1990, 31, 3267. (o) Chackahamannil, S.; Fett, N.; Kirkup, M.; Afonso, A.; Ganguly, A. K. J. Org. Chem. 1988, 53, 450. (p) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161. For an alternative synthesis of β-lactams involving intramolecular alkylation, see: (q) Wasserman, H. H.; Hlasta, D. J. Tetrahedron Lett. 1979, 20, 549.
69. For recent reviews on the synthesis of thienamycin (1) and related materials, see: (a) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A-ur, Ed.; Elsevier Science: Amsterdam, 1989; Vol. 4. (c) Bateson, J. H. In Progress in Heterocyclic Chemistry; Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1991; Vol. 3. See also: (d) Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098 and references cited therein. (e) Grieco, P. A.; Flynn, D. L.; Zelle, R. E. J. Am. Chem. Soc. 1984, 106, 6414. (f) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498. (g) Evans, D. A.; Sjogren, E. B Tetrahedron Lett. 1986, 27, 4961. (h) Corbett, D. F.; Coulton, S.; Southgate, R J. Chem. Soc., Perkin Trans. 1 1982, 3011 and references cited therein. (i) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986, 27, 3119. (j) Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796. (k) Shono, T.; Kise, N.; Sanda, F.; Ohi, S.; Yoshioka K. Tetrahedron Lett. 1989, 30, 1253. (l) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498 and references cited therein. (m) Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807. (n) Georg, G. I.; Akgun, E. Tetrahedron Lett. 1990, 31, 3267. (o) Chackahamannil, S.; Fett, N.; Kirkup, M.; Afonso, A.; Ganguly, A. K. J. Org. Chem. 1988, 53, 450. (p) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161. For an alternative synthesis of β-lactams involving intramolecular alkylation, see: (q) Wasserman, H. H.; Hlasta, D. J. Tetrahedron Lett. 1979, 20, 549.
70. (a) Lockwood, R. F.; Nicholas, K M. Tetrahedron Lett. 1977, 18, 4163.
71. (b) Nicholas, K. M.; Nestle, M. O.; Seyferth, D. In Transition Metal Organometallics in Organic Synthesis; Alper, H., Ed.; Academic Press: New York, 1978; Vol. 2, p 1.
72. (c) Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128.
73. (d) Nicholas, K. M.; Mulvaney, M.; Bayer, M. J. Am. Chem. Soc. 1980, 102, 2508.
74. (e) Hodes, H. D.; Nicholas, K. M. Tetrahedron Lett. 1978, 19, 4349.
75. (f) Bramwell, A. F.; Crombie, L.; Knight, M. H. Chem Ind. (London) 1965, 1265 and references cited therein.
76. (g) Saha, M.; Bogby, B.; Nicholas, K. M. Tetrahedron Lett. 1986, 27, 915.
77. (h) Schreiber, S. L.; Klimas, M. T.; Sammakia, T. J. Am. Chem. Soc. 1987, 109, 5749.
78. (a) Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203.
79. (b) Benalil, A.; Roby, P.; Carboni, B.; Vaultier, M. Synthesis, 1991, 787.
80. (a) Pappo, R.; Allen, D. S., Jr.; Lemieux, R. U.; Johnson, W. S. J. Org. Chem. 1956, 21, 478.
81. (b) Moriarty, R. M.; Penmasta, R.; Awasthi, A. K.; Prakash, I. J. Org. Chem. 1988, 53, 6164 and references cited therein.
82. For previous papers in this series see: (a) Jacobi, P. A.; Guo, J. Tetrahedron Lett. 1995, 36, 2717. (b) Jacobi, P. A.; Guo, J.; Zheng, W. Tetrahedron Lett. 1995, 36, 1197. (c) Jacobi, P. A.; Brielmann, H. L.; Hauck, S. I. Tetrahedron Lett. 1995, 36, 1193. (d) Jacobi, P. A.; Zheng, W. Tetrahedron Lett. 1993, 34, 2581. (e) Jacobi, P. A.; Zheng, W. Tetrahedron Lett. 1993, 34, 2580. (f) Jacobi, P. A.; Rajeswari, S. Tetrahedron Lett. 1992, 33, 6231; (g) 1992, 33, 6235. (g) Jacobi, P. A; DeSimone, R. W. Tetrahedron Lett. 1992, 33, 6239.
83. For previous papers in this series see: (a) Jacobi, P. A.; Guo, J. Tetrahedron Lett. 1995, 36, 2717. (b) Jacobi, P. A.; Guo, J.; Zheng, W. Tetrahedron Lett. 1995, 36, 1197. (c) Jacobi, P. A.; Brielmann, H. L.; Hauck, S. I. Tetrahedron Lett. 1995, 36, 1193. (d) Jacobi, P. A.; Zheng, W. Tetrahedron Lett. 1993, 34, 2581. (e) Jacobi, P. A.; Zheng, W. Tetrahedron Lett. 1993, 34, 2580. (f) Jacobi, P. A.; Rajeswari, S. Tetrahedron Lett. 1992, 33, 6231; (g) 1992, 33, 6235. (g) Jacobi, P. A; DeSimone, R. W. Tetrahedron Lett. 1992, 33, 6239.
84. For previous papers in this series see: (a) Jacobi, P. A.; Guo, J. Tetrahedron Lett. 1995, 36, 2717. (b) Jacobi, P. A.; Guo, J.; Zheng, W. Tetrahedron Lett. 1995, 36, 1197. (c) Jacobi, P. A.; Brielmann, H. L.; Hauck, S. I. Tetrahedron Lett. 1995, 36, 1193. (d) Jacobi, P. A.; Zheng, W. Tetrahedron Lett. 1993, 34, 2581. (e) Jacobi, P. A.; Zheng, W. Tetrahedron Lett. 1993, 34, 2580. (f) Jacobi, P. A.; Rajeswari, S. Tetrahedron Lett. 1992, 33, 6231; (g) 1992, 33, 6235. (g) Jacobi, P. A; DeSimone, R. W. Tetrahedron Lett. 1992, 33, 6239.
85. For previous papers in this series see: (a) Jacobi, P. A.; Guo, J. Tetrahedron Lett. 1995, 36, 2717. (b) Jacobi, P. A.; Guo, J.; Zheng, W. Tetrahedron Lett. 1995, 36, 1197. (c) Jacobi, P. A.; Brielmann, H. L.; Hauck, S. I. Tetrahedron Lett. 1995, 36, 1193. (d) Jacobi, P. A.; Zheng, W. Tetrahedron Lett. 1993, 34, 2581. (e) Jacobi, P. A.; Zheng, W. Tetrahedron Lett. 1993, 34, 2580. (f) Jacobi, P. A.; Rajeswari, S. Tetrahedron Lett. 1992, 33, 6231; (g) 1992, 33, 6235. (g) Jacobi, P. A; DeSimone, R. W. Tetrahedron Lett. 1992, 33, 6239.
86. For previous papers in this series see: (a) Jacobi, P. A.; Guo, J. Tetrahedron Lett. 1995, 36, 2717. (b) Jacobi, P. A.; Guo, J.; Zheng, W. Tetrahedron Lett. 1995, 36, 1197. (c) Jacobi, P. A.; Brielmann, H. L.; Hauck, S. I. Tetrahedron Lett. 1995, 36, 1193. (d) Jacobi, P. A.; Zheng, W. Tetrahedron Lett. 1993, 34, 2581. (e) Jacobi, P. A.; Zheng, W. Tetrahedron Lett. 1993, 34, 2580. (f) Jacobi, P. A.; Rajeswari, S. Tetrahedron Lett. 1992, 33, 6231; (g) 1992, 33, 6235. (g) Jacobi, P. A; DeSimone, R. W. Tetrahedron Lett. 1992, 33, 6239.
87. For previous papers in this series see: (a) Jacobi, P. A.; Guo, J. Tetrahedron Lett. 1995, 36, 2717. (b) Jacobi, P. A.; Guo, J.; Zheng, W. Tetrahedron Lett. 1995, 36, 1197. (c) Jacobi, P. A.; Brielmann, H. L.; Hauck, S. I. Tetrahedron Lett. 1995, 36, 1193. (d) Jacobi, P. A.; Zheng, W. Tetrahedron Lett. 1993, 34, 2581. (e) Jacobi, P. A.; Zheng, W. Tetrahedron Lett. 1993, 34, 2580. (f) Jacobi, P. A.; Rajeswari, S. Tetrahedron Lett. 1992, 33, 6231; (g) 1992, 33, 6235. (g) Jacobi, P. A; DeSimone, R. W. Tetrahedron Lett. 1992, 33, 6239.
88. For previous papers in this series see: (a) Jacobi, P. A.; Guo, J. Tetrahedron Lett. 1995, 36, 2717. (b) Jacobi, P. A.; Guo, J.; Zheng, W. Tetrahedron Lett. 1995, 36, 1197. (c) Jacobi, P. A.; Brielmann, H. L.; Hauck, S. I. Tetrahedron Lett. 1995, 36, 1193. (d) Jacobi, P. A.; Zheng, W. Tetrahedron Lett. 1993, 34, 2581. (e) Jacobi, P. A.; Zheng, W. Tetrahedron Lett. 1993, 34, 2580. (f) Jacobi, P. A.; Rajeswari, S. Tetrahedron Lett. 1992, 33, 6231; (g) 1992, 33, 6235. (g) Jacobi, P. A; DeSimone, R. W. Tetrahedron Lett. 1992, 33, 6239.
89. For previous papers in this series see: (a) Jacobi, P. A.; Guo, J. Tetrahedron Lett. 1995, 36, 2717. (b) Jacobi, P. A.; Guo, J.; Zheng, W. Tetrahedron Lett. 1995, 36, 1197. (c) Jacobi, P. A.; Brielmann, H. L.; Hauck, S. I. Tetrahedron Lett. 1995, 36, 1193. (d) Jacobi, P. A.; Zheng, W. Tetrahedron Lett. 1993, 34, 2581. (e) Jacobi, P. A.; Zheng, W. Tetrahedron Lett. 1993, 34, 2580. (f) Jacobi, P. A.; Rajeswari, S. Tetrahedron Lett. 1992, 33, 6231; (g) 1992, 33, 6235. (g) Jacobi, P. A; DeSimone, R. W. Tetrahedron Lett. 1992, 33, 6239.
90. Evans, D. A.; Britton, T. C ; Ellman, J. A. Tetrahedron Lett. 1987, 28, 6141.
91. We are grateful to Ms. Gayle Schulte, of Yale University, for carrying out an X-ray analysis of acetylenic acid 25c.
92. (a) Tanner, D.; Somfai, P. Tetrahedron 1988, 44, 619.
93. See also: (b) Shono, T.; Rise, N.; Sanda, F.; Ohi, S.; Yoshioka, K. Tetrahedron Lett. 1989, 30, 1253.
94. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem Soc. 1981, 103, 2127.
95. Chiba, T.; Nakia, T. Tetrahedron Lett. 1985, 26, 4647.
96. We are grateful to Professor Paul Grieco, of Indiana University, for providing an NMR spectra of (=)-63 (cf. ref 12e).