Preliminary communication

Thiazabicycloheptenones. Synthesis of Bicyclic Thiazoline Azetidinone Derivatives

S. Kukolja ; The Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana, U.S.A.
S. R. Lammert ; The Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana, U.S.A.

Abstract

Chlorinolysis of the S1-C5 bond in penicillin G and the subsequent
cyclization of the obtained product to the thiazabicycloheptenone
is described. The intermediate azetidinone imidoyl
chloride III is prepared by treatment of the olefinic azetidinone II
with phosphorous pentachloride. Cyclization of III is effected
with thioacetate anion or hydrogen sulfide in the presence .of
triethylamine. The structure and chirality of thiazabicycloheptenone IV
were established by spectral data as well as by comparison with
the sample prepared by an independent manner3 from penicillin
G sulfoxide.

Keywords

Hrčak ID:

197278

URI

https://hrcak.srce.hr/197278

Publication date:

15.7.1972.

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