Current time in Korea 01:16 Nov 19 (Tue) Year 2019 KCS KCS Publications
KCS Publications
My Journal Log In Register
HOME > Search > Browsing(BKCS) > Archives

Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 35, Number 10
BKCSDE 35(10)
October 20, 2014 

 
Title
Studies on the Design and Synthesis of New Monocyclic β-Lactams Containing Substructures of Penicillin G
Author
Sang Hyup Lee
Keywords
Monocyclic β-lactams, 3-mercaptobutanoate, Acetylthio, Azetidinone
Abstract
The studies on design and synthesis of new monocyclic β-lactam esters 4(R/S)-(1'-methoxycarbonylpropyl- 2'(R/S)-thio)-3(R)-phenylacetamidoazetidin-2-one (3a) and 4(R/S)-(1'-methoxycarbonyl-2'-methyl-propyl-2'- thio)-3(R)-phenylacetamidoazetidin-2-one (3b) were described. Compounds 3a and 3b were specifically designed to retain all penicillin substructures except the bicyclic system, which would be conceived by cleaving the C(3)–N(4) bond of penicillin G. Compounds 3a and 3b are of particular interest in the context of the structural elucidation of monocyclic β-lactams originated from penicillin. Key intermediates, β-mercapto esters 6a and 6b, were synthesized from conjugate acids 4a and 4b using three-step synthetic sequences, respectively, and 4(S)-acetoxy-3(S)-phenylacetamidoazetidin-2-one (7) was obtained from the degradation of penicillin G. Reactions of 6a and 6b with 7, thus obtained, provided the target compounds 3a and 3b, respectively.
Page
2990 - 2994
Full Text
PDF