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PANGAEA Supplementary Data
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doi:10.1016/S0040-4039(00)83988-X    
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Copyright © 1986 Published by Elsevier Science Ltd. All rights reserved.

A stereocontrolled route to optically active 1-methyl carbapenems

Pamela Brown, * and Robert Southgate

Beecham Pharmaceuticals Research Division, Brockham Park, Betchworth, Surrey, RH3 7AJ, U.K.


Received 21 October 1985. 
Available online 8 March 2001.

Abstract

Using a stereoselective carbene insertion reaction to form the β-lactam ring, optically active 1-methyl carbapenems have been prepared.

References

R.J. Ponsford and R. Southgate J. Chem. Soc. (1979), p. 846 Chem. Commun. . Full Text via CrossRef

A similar intermediate has recently been prepared in racemic form by workers at Merck Sharp and Dohme; D.H. Shih, J.A. Fayter, L.D. Cama, B.G. Christensen and J. Hirshfield Tetrahedron Lett. 26 (1985), p. 583. Abstract | PDF (242 K) | View Record in Scopus | Cited By in Scopus (6)

All compounds were characterised by infra-red and 250MHz 1H n.m.r. spectra plus mass spectral and/or microanalytical evidence. Some selected physical data for compound (3) and its C-5 epimer are as follows; (3): δ(CDCl3) 0.92 (3H, d, Image 6.0Hz, 5-CH3), 1.32 (3H, d, Image 6.0 Hz, 9-CH3), 2.79 (1H, dd, Image 5.0, 1.5Hz, 7-H), 3.14 (1H, dd, Image , 1.5, 9.8 Hz, 6-H), C-5 epimer (β-methyl): δ(CDCl3) 1.13 (d, Image 7Hz, 5-CH3), 1.30 (3H, d, Image 7Hz, 9-CH3), 3.03 (1H, dd, Image 6.6, 2.0Hz, 7-H), 3.75 (1H, dd, Image 5.1, 2.0 Hz, 6-H).

E. Felder, D. Pitrè and S. Boveri Helv. Chim. Acta 12 (1969), p. 329. Full Text via CrossRef

K. BalenoviImage and M. Bregant Croat. Chem. Acta. 32 (1960), p. 57.

A.J.G. Baxter, P. Davis, R.J. Ponsford and R. Southgate Tetrahedron Lett. 21 (1980), p. 5071. Abstract | PDF (195 K) | View Record in Scopus | Cited By in Scopus (5)
M.J. Basker, R.J. Boon, S.J. Box, A.G. Brown, P. Davis, R.J. Ponsford, R. Southgate and S.R. Spear J. Antibiotics 36 (1983), p. 1357. View Record in Scopus | Cited By in Scopus (0)


Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 247-250
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