The syntheses of functionalized 2-alkenyl and alkynyl-1-β- methyl-carbapenems via the Stille cross-coupling reaction

Tetrahedron Letters

Volumn 39, Issue 14, 1998, Pages 1865-1868

  Dykstra, Kevin D ^a   DiNinno, Frank ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAPENEM DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; CHEMICAL REACTION; DERIVATIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0032473902     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00121-X     Document Type: Article

References (32)

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20. 3), δ: 0.57 (q, J= 5.0 Hz, 6H), 0.91 (t, J= 7.8 Hz, 1H), 1.19 (d, J=7.4 Hz, 3H), 1.26 (d, J= 6.2 Hz, 3H), 3.19 (dd, J= 2.7, 3.4 Hz, 1H), 3.31-3.37 (m, 1H), 4.15 (dd, J= 2.7, 6.7 Hz, 1H), 4.21 (m, 1H), 4.29 (bd, J= 4.8 Hz, 2H), 5.23-5.45 (ABq, J= 13.9 Hz, 2H), 6.14 (dt, J= 5.3 Hz, 1H), 7.27 (d, J=36.3 Hz, 1H), 7.64 (d, J= 8.8 Hz, 2 H), 8.19 (d, J= 8.8 Hz, 2H).
21. 9. The analogous Stille cross-coupling with a carbacephem vinyl triflate was reported concurrently with the preparation of this manuscript. White, R. E.; et. al Abstracts of the 37th Interscience Conference on Antimicrobial Agents and Chemotherapy, Toronto, Ontario, September 28-October 1, 1997, F193.
22. 10. Thanks to K. Wildonger who provided the chromatographed (Z)-isomer.
23. 3), δ: 0.56-0.62 (m, 6H), 0.92-0.96 (t, J= 8.0, 7.9 Hz, 9H), 1.13 (d, J=7.5 Hz, 3H), 1.27 (d, J= 6.1 Hz, 3H), 3.22-3.29 (m, 2H), 4.18 (m, 2H), 4.45 (dd, J= 5.9, 7.4 Hz, 1H), 4.56 (d, J= 6.1, 7.0 Hz, 1H), 6.34 (m, 1H), 6.42 (d, J= 10.0 Hz, 1H).
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25. 3), δ: 0.78 (t, J= 7.3 Hz, 9H), 0.91 (t, J= 8.1, 7.2 Hz, 6H), 1.24-1.27 (m, 6H), 1.53-1.58 (m, 6H), 4.77 (d, J= 6.8 Hz, 2H), 6.27 (d, J= 9.1 Hz, 1H), 6.77 (p, J= 4.1 Hz, 1H), 7.38 (m, 3H), 7.63-7.68 (m, 4H), 8.13 (dd, J=6.8, 3.1Hz, 2H).
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32. 3), δ: 0.59-0.68 (m, 12H), 0.91-0.99 (m, 18H), 1.24 (d, J=6.4 Hz, 3H), 1.26 (d, J= 6.2 Hz, 3H), 3.19-3.22 (m, 1H), 3.32 (dd, J= 3.2, 2.6 Hz, 1H), 4,25-4.32 (m, 2H), 4.53 (s, 2H), 5.29-5.47 (ABq, J= 14.0 Hz, 2H), 7.66 (d, J= 9.0 Hz, 2H), 8.22 (d, 7= 8.9 Hz, H).