Asymmetric radical cyclization leading to β-lactams: Stereoselective synthesis of chiral key intermediates for carbapenem antibiotics PS-5 and thienamycin

Tetrahedron

Volumn 52, Issue 2, 1996, Pages 489-502

  Ishibashi, Hiroyuki ^a,b   Kameoka, Chisato ^a   Kodama, Kazuya ^a   Ikeda, Masazumi ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^b KANAZAWA UNIVERSITY   (Japan)

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; CARBAPENEM DERIVATIVE; THIENAMYCIN;

ARTICLE; CHIRALITY; CYCLIZATION; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030026894     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00902-7     Document Type: Article

References (49)

1. For reviews on the stereochemical control in radical addition reactions in acyclic and cyclic systems, see: Giese, B. Angew. Chem. Int. Ed. Engl. 1989, 28, 969. Porter, N.A.; Giese, B.; Curran, D.P. Acc. Chem. Res. 1991, 24, 296. Smadja, W. Synlett 1994, 1.
2. For reviews on the stereochemical control in radical addition reactions in acyclic and cyclic systems, see: Giese, B. Angew. Chem. Int. Ed. Engl. 1989, 28, 969. Porter, N.A.; Giese, B.; Curran, D.P. Acc. Chem. Res. 1991, 24, 296. Smadja, W. Synlett 1994, 1.
3. For reviews on the stereochemical control in radical addition reactions in acyclic and cyclic systems, see: Giese, B. Angew. Chem. Int. Ed. Engl. 1989, 28, 969. Porter, N.A.; Giese, B.; Curran, D.P. Acc. Chem. Res. 1991, 24, 296. Smadja, W. Synlett 1994, 1.
4. For a review on the stereochemistry of radical cyclizations, see: RajanBabu, T.V. Acc. Chem. Res. 1991, 24, 139.
5. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am..Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Gulndon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35, 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. See also ref 4.
6. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am..Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Gulndon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35, 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. See also ref 4.
7. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am..Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Gulndon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35, 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. See also ref 4.
8. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am..Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Gulndon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35, 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. See also ref 4.
9. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am..Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Gulndon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35, 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. See also ref 4.
10. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am..Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Gulndon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35, 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. See also ref 4.
11. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am..Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Gulndon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35, 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. See also ref 4.
12. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am..Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Gulndon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35, 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. See also ref 4.
13. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am..Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Gulndon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35, 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. See also ref 4.
14. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am..Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Gulndon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35, 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. See also ref 4.
15. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am..Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Gulndon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35, 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. See also ref 4.
16. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am..Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Gulndon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35, 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. See also ref 4.
17. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Gieb, S.V.; Lin, C.-H. Heterocycles, 1994, 57, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199.
18. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Gieb, S.V.; Lin, C.-H. Heterocycles, 1994, 57, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199.
19. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Gieb, S.V.; Lin, C.-H. Heterocycles, 1994, 57, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199.
20. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Gieb, S.V.; Lin, C.-H. Heterocycles, 1994, 57, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199.
21. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Gieb, S.V.; Lin, C.-H. Heterocycles, 1994, 57, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199.
22. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Gieb, S.V.; Lin, C.-H. Heterocycles, 1994, 57, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199.
23. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Gieb, S.V.; Lin, C.-H. Heterocycles, 1994, 57, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199.
24. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Gieb, S.V.; Lin, C.-H. Heterocycles, 1994, 57, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199.
25. Ishibashi, H.; Kameoka, C.; Iriyama, H.; Kodama, K.; Sato, T.; Ikeda, M. J. Org. Chem. 1995, 60, 1276.
26. The diastereoselective formation of (3S,4S)-azetidinone 2a from 1 may reflect only the chirality of the oxygen functionality at the side chain (not bromine atom) of 1, since no asymmetric induction was observed for the cyclization of (2S)-2-chloro-N-(p-methoxybenzyl)-N-[2,2-bis(phenylthio)ethenyl]-propanamide leading to 1-(p-methoxybenzyl)-3-methyl-4-[bis(phenylthio)methyl]-2-azetidinone (unpublished results).
27. For a preliminary account of a portion of this work, see: Ishibashi, H.; Kameoka, C.; Sato, T.; Ikeda, M. Synlett 1994, 445.
28. 3, 60 MHz) δ 1.47 (d, J = 7 Hz, 3 H), 4.44 (quint, J = 7 Hz, 1 H), 5.1-5.7 (br, 1 H), 6.9-7.7 (m, 16 H).
29. Gutierrez, C.G.; Stringham, R.A.; Nitasaka, T.; Glasscock, K.G. J. Org. Chem. 1980, 45, 3393.
30. Kostyanovsky, R.G.; Gella, I.M.; Markov, V.I.; Samojlova, Z.E. Tetrahedron 1974, 30, 39.
31. Okamura, K.; Hirata, S.; Koki, A.; Hori, K.; Shibamoto, N.; Okumura, Y.; Okabe, M.; Okamoto, T.; Kouno, K.; Fukugawa, Y.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1979, 32, 262. Sakamoto, M.; Iguchi, H.; Okamura, K.; Hori, S.; Fukagawa, Y.; Ishikura, T.; J. Antibiot. 1979, 32, 272. Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796.
32. Okamura, K.; Hirata, S.; Koki, A.; Hori, K.; Shibamoto, N.; Okumura, Y.; Okabe, M.; Okamoto, T.; Kouno, K.; Fukugawa, Y.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1979, 32, 262. Sakamoto, M.; Iguchi, H.; Okamura, K.; Hori, S.; Fukagawa, Y.; Ishikura, T.; J. Antibiot. 1979, 32, 272. Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796.
33. Okamura, K.; Hirata, S.; Koki, A.; Hori, K.; Shibamoto, N.; Okumura, Y.; Okabe, M.; Okamoto, T.; Kouno, K.; Fukugawa, Y.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1979, 32, 262. Sakamoto, M.; Iguchi, H.; Okamura, K.; Hori, S.; Fukagawa, Y.; Ishikura, T.; J. Antibiot. 1979, 32, 272. Yamamoto, K.; Yoshioka, T.; Kato, Y.; Shibamoto, N.; Okamura, K.; Shimauchi, Y.; Ishikura, T. J. Antibiot. 1980, 33, 796.
34. In general, the radical cyclizations herein examined proceeded with much higher diastereoselectivity in boiling toluene than in boiling benzene. However, the yields in toluene were usually lower than those in benzene. No simple explanation for the results can be offered at the present time.
35. Peterson, D.J. J. Org. Chem. 1968, 33, 780. Hudrick, P.F.; Peterson, D.; Rona, R.J. J. Org. Chem. 1975, 40, 2263.
36. Peterson, D.J. J. Org. Chem. 1968, 33, 780. Hudrick, P.F.; Peterson, D.; Rona, R.J. J. Org. Chem. 1975, 40, 2263.
37. Okano, K.; Izawa, T.; Ohno, M. Tetrahedron Lett. 1983, 24, 217.
38. Favara, D.; Omodei-sale, A.; Consonni, P.; Depaoli, A. Tetrahedron Lett. 1982, 23, 3105.
39. 3)].
40. 3)].
41. 3)].
42. For a review on the synthesis of PS-5 and related compounds, see: Palomo, C. In Recent Progress in the Chemical Synthesis of Antibiotics; Lukacs, G.; Ohno, M., Ed.; Springer-Verlag: Berlin-Heidelberg, 1990; pp 565-612.
43. The bromide bearing a mismatched pair of chiral inductors, e. g., (2S,3R)-3-acetoxy-2-bromo congener of 28, gave a 57:43 mixture of two diastereoisomers of 3-[(R)-1-acetoxyethyl]-1-[(S)-1-phenylethyl]-4-[bis(phenylthio)methyl]-2- azetidinone.
44. Albers-Schonberg, G.; Arison, B.H.; Hensens, O.D.; Hirshfield, J.; Hoogsteen, K.; Kaczka, E.S.; Rhodes, R.E.; Kahan, J.S.; Kahan, F.M.; Ratcliffe, R.W.; Walton, E.; Ruswinkle, L.J.; Morin, R.B.; Christensen, B.C. J. Am. Chem. Soc. 1978, 100, 6491. Kahan, J.S.; Kahan, F.M.; Goegelman, R.; Currie, S.A.; Jackson, M.; Stapley, E.O.; Miller, T.W.; Miller, A.K.; Hendlin, C.; Mochales, S.; Hernandez, S.; Woodruff, H.B.; Birnbaum, J. J. Antibiot. 1979, 32, 1.
45. Albers-Schonberg, G.; Arison, B.H.; Hensens, O.D.; Hirshfield, J.; Hoogsteen, K.; Kaczka, E.S.; Rhodes, R.E.; Kahan, J.S.; Kahan, F.M.; Ratcliffe, R.W.; Walton, E.; Ruswinkle, L.J.; Morin, R.B.; Christensen, B.C. J. Am. Chem. Soc. 1978, 100, 6491. Kahan, J.S.; Kahan, F.M.; Goegelman, R.; Currie, S.A.; Jackson, M.; Stapley, E.O.; Miller, T.W.; Miller, A.K.; Hendlin, C.; Mochales, S.; Hernandez, S.; Woodruff, H.B.; Birnbaum, J. J. Antibiot. 1979, 32, 1.
46. Hirai, K.; Iwano, Y.; Fujimoto, K. Tetrahedron Lett. 1982, 23, 4025.
47. Hirai, K.; Iwano, Y.; Fujimoto, K. Tetrahedron Lett. 1983, 24, 3251.
48. For a review on the enantioselective syntheses of (+)-thienamycin, see: Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729.
49. 3 solution unless otherwise noted with tetramethylsilane as an internal standard. For other general experimental details, see ref 5.