Concepedia

A FACILE, STEREOCONTROLLED ENTRY TO KEY INTERMEDIATES FOR THIENAMYCIN SYNTHESIS FROM ETHYL (<i>S</i>)-3-HYDROXYBUTANOATE

Toshiyuki Chiba, Masako Nagatsuma, Takeshi Nakai

Chemistry Letters · 1985 · 54 citations · 14 references

DOI

Concepts

Abstract

Abstract A new synthetic approach to optically active key intermediates for thienamycin synthesis is described which involves the highly stereocontrolled transformation of the 2-azetidinone obtained via the condensation of ethyl (S)-3-hydroxybutanoate with the N-silylimine of trimethylsilylpropynal.

References

14

A stereocontrolled synthesis of (+)-thienamycin

T. N. SALZMANN, Ronald W. Ratcliffe, B. G. CHRISTENSEN et al. · Journal of the American Chemical Society · 1980 · 388 citations

, , +6

A novel synthesis of the carbapen-2-em ring system

Ronald W. Ratcliffe, T. N. SALZMANN, B. G. CHRISTENSEN · Tetrahedron Letters · 1980 · 163 citations

, , +13

Synthesis of Carbapenem Antibiotics

Tetsuji Kametani, Keiichiro Fukumoto, Masataka Ihara · Heterocycles · 1982 · 130 citations · Full text

, , +3

Total synthesis of thienamycin: a new approach from aspartic acid

Paul J. Reider, Edward J. J. Grabowski · Tetrahedron Letters · 1982 · 126 citations

, , +7

A practical synthesis of (±)-thienamycin

David G. Melillo, I. Shinkai, T. Liu et al. · Tetrahedron Letters · 1980 · 126 citations

, , +6