Croatica Chemica Acta, Vol. 44 No. 2, 1972.
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
Publication date:
15.7.1972.
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