The Penems, a New Class of β-Lactam Antibiotics. 3. Synthesis of Optically Active 2-Methyl-(5R)-penem-3-carboxylic Acid

Journal of the American Chemical Society

Volumn 101, Issue 21, 1979, Pages 6301-6305

  Ernest, I ^a   Gosteli, J ^a   Woodward, R B ^a  

^a (The Former) Woodward Research Institute   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYL 3 PENEMCARBOXYLIC ACID; ANIMAL EXPERIMENT; BACTERIUM; DRUG ANALYSIS; DRUG COMPARISON; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; INFRARED SPECTROMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; POLARIMETRY; STRUCTURE ACTIVITY RELATION; THEORETICAL STUDY; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0018568810     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00515a025     Document Type: Article

References (6)

1. I. Ernest, J. Gosteli, C.W. Greengrass, W. Holick, D.E. Jackman, H.R. Pfaendler, and R.B. Woodward, J. Am. Chem. Soc., 100, 8214 (1978).
2. J.P. Clayton, J. Chem. Soc. C., 2123 (1969).
3. E. Evrard, M. Claesen, and H. Vanderhaege, Nature (London), 201, 1124 (1964).
4. As a byproduct, the seven-membered cyclic compound i was isolated by chromatography of the crude hydrogenation product. Stoodley et al. (J.P. Clayton, R. Southgate, B.G. Ramsay, and R.J. Stoodley, J. Chem. Soc. C., 2089 (1970)
5. T. Kamiya, T. Teraji, M. Hashimoto, O. Nakaguchi, and T. Oku, Tetrahedron Lett., 3001 (1973)
6. T. Kamiya, T. Teraji, M. Hashimoto, O. Nakaguchi, and T. Oku, Tetrahedron Lett., 2 230 372 (1973)