Solid-phase total synthesis of 1-β-methylcarbapenem

Chinese Chemical Letters

Volumn 14, Issue 1, 2003, Pages 6-8

  Lei, Ming ^a   Ma, Cheng ^a   Wang, Yan Guang ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Antibiotics; Carbapenem; Solid phase; Synthesis of lactam

Indexed keywords

1 BETA METHYLCARBAPENEM; CARBAPENEM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; SOLID;

EID: 0037263234     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (14)

1. (a) F. Z. Dorwald, Organic Synthesis on Solid Phase, WILEY-VCH, Singapore, 2000.
2. (b) B. A. Lorsbach, M. J. Kurth, Chem. Rev., 1999, 99, 1549.
3. (a) K. Kondo, M. Seki, T. Kuroda, T. Yamanaka, T. Iwasaki, J. Org. Chem., 1997, 62, 2877.
4. (b) K. Kondo, M. Seki, T. Kuroda, T. Yamanaka, T. Iwasaki, J. Org. Chem., 1995, 60, 1096.
5. (c) M. Mori, Y. Kozawa, M. Nishida, M. Kanamaru, K. Onozuka, M. Takimoto, Org. Lett., 2000, 2, 3245.
6. (d) Y. Kozawa, M. Mori, Tetrahedron Lett., 2002, 43, 111.
7. (e) H. R. Pfaendler, R. Weishaupt, H. Meffert, Bioorg. Med. Chem. Lett., 2000, 10, 1389.
8. (f) T. Nishimura, J. Igarashi, A. Sasaki, M. Sunagawa, Bioorg. Med. Chem., 1998, 6, 367.
9. (g) M. Kume, T. Kubota, Y. Iso, Tetra. Lett. 1995, 36, 8043.
10. (h) S. Roland, J. O. Durand, M. Savignac, Tetrahedron Lett. 1995, 36, 3007.
11. Y. H. Hu, J. A. Porco, Jr., J. W. Labadic, O. W. Gooding, J. Org. Chem., 1998, 63, 4518.
12. T. N. Salzmann, R. W. Ratcliffe, B. G. Christensen, F. A. Bouffard, J. Am. Chem. Soc., 1980, 102, 6163.
13. 3, δ ppm): 7.53-7.38 (m, 5H), 5.99 (m, 1H), 5.49-5.27(m, 2H), 4.88-4.71(m, 2H), 4.19 (m, 1H), 4.13 (dd, 1H, J=1.6, 1.8Hz), 3.18 (dd, 1H, J=4.5, 2.0Hz), 3.06 (m, 1H), 2.04 (bs, 1H), 1.28 (d, 3H, J-6.2Hz), 0.96 (d, 3H, J=7.2Hz).
14. The spectral data are correspondent with the following literature data: M. Seki, K. Kondo, T. Kuroda, T. Yamanaka, T. Iwasaki, Synlett 1995, 609.