Stereospecific Conversion of Penicillin to Thienamycin

Journal of the American Chemical Society

Volumn 103, Issue 22, 1981, Pages 6765-6767

  Karady, Sandor ^a   Amato, Joseph S ^a   Reamer, Robert A ^a   Weinstock, Leonard M ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 AMINOPENICILLANIC ACID; THIENAMYCIN;

DRUG ANALYSIS; DRUG IDENTIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; PRELIMINARY COMMUNICATION; PROTON NUCLEAR MAGNETIC RESONANCE; THEORETICAL STUDY;

EID: 0019834818     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00412a048     Document Type: Article

References (17)

1. Melillo, D. G.; Shinkai, I.; Liu, T.; Ryan, K.; Sletzinger, M. Tetrahedron Lett. 1980, 2783.
2. Saltzman, T. N.; Ratcliffe, R.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161.
3. Johnston, D. B. R.; Schmitt, S. M.; Bouffard, F. A.; Christensen, B. G. J. Am. Chem. Soc. 1978,100, 313.
4. Kametami, T.; Huang, S.-P.; Suzuki, J.; Yokohama, S.; Shara, M. Heterocycles 1979, 12, 1301.
5. Sheehan, J. C.; Lo, Y. S.
6. J. Org. Chem. 1973, 38, 3227.
7. Sheehan, J. C.; Chacko, E.; Lo, Y. S.; Ponzi, D. R.; Sato, E. J. Org. Chem. 1978, 43, 4856.
8. These compounds were first produced by a nonstereospecific method. Chromatographic separation of the diastereomers by the method of: DiNinno, F.; Beattie, T. R.; Christensen, B. G. J. Org. Chem. 1977, 42, 2960. We thank Dr. DiNinno for a sample of 3.
9. Brain, E. G.; McMillan, I.; Nayler, J. H. C.; Southgate, R.; Tolliday, P. J. Chem. Soc., Perkin Trans. I 1975, 562.
10. Brain, E. G.; Elington, A. J.; Nayler, J. H. C.; Pearson, M. J.; Southgate, R. J. Chem. Soc., Perkin Trans. 1 1976, 447.
11. Kukolja, S. J. Am. Chem. Soc. 1971, 93, 6267.
12. Chan, T.; Brownbridg, P. J. Am. Chem. Soc. 1980,102, 3534. We thank Professor Chan for a detailed procedure for the preparation of the analogous methyl ester. In our case, LiHMDS and Me3SiCl were used and the procedure had to be repeated twice to complete the formation of 6b. On attempted distillation, O to C silyl rearrangement took place.
13. Danishefsky, S.; Singh, R.; Gammill, R. B.
14. J. Org. Chem. 1978, 43, 380.
15. Hazen, G. G.; Weinstock, L. M.; Connell, R.; Bollinger, F. W. Synth. Commun., submitted for publication.
16. Ratcliffe, R. W.; Saltzmann, T. N.; Christensen, G. B. Tetrahedron Lett. 1980, 31.
17. Sletzinger, M.; Liu, T.; Reamer, R. A.; Shinkai, I. Tetrahedron Lett. 1980, 21, 4221.