Synthesis and stereochemistry of chiral azetidin-2-ones and azetidine-2-thiones. 3. Stereodirected construction of the β-lactam fragment of the thienamycin molecule

Authors

  • Н. Н. Романова M. V. Lomonosov Moscow State University, Moscow 119899
  • Т. Г. Талло M. V. Lomonosov Moscow State University, Moscow 119899
  • Ю. Г. Бyндель M. V. Lomonosov Moscow State University, Moscow 119899

Abstract

It has been shown possible to introduce an α-hydroxyethyl group trans-stereospecifically into position 3′ of 4-methyl-1-(α-methyl-benzyl)azetidin-2-one. The stereochemistry of the asymmetric centers C(3′), C(3), and C(4) of the diastereoisomers of the 3-α-hydroxyethyl derivative obtained in larger amount and of the corresponding three adjacent chiral centers C(8), C(6), and C(5) in thienamycin are the same.

How to Cite
Romanova, N. N.; Tallo, T. G.; Bundel, Yu. G.  Chem. Heterocycl. Compd. 1995, 31, 223. [Khim. Geterotsikl. Soedin. 1995, 254.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01169684

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Published

1995-02-25

Issue

No. 2 (1995)

Section

Original Papers