Title of article
Synthesis of a novel thiabicyclo[3.2.0]heptan-6-one analogue of penicillin
Author/Authors
Domnic H Martyres، نويسنده , , Jack E. Baldwin، نويسنده , , Robert M. Adlington، نويسنده , , Victor Lee، نويسنده , , Mike R Probert، نويسنده , , David J Watkin، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2001
Pages
9
From page
4999
To page
5007
Abstract
Synthesis of (1SR, 4SR, 5SR, 7RS)-7-(tert-butoxycarbonylamino)-2-thiabicyclo[3.2.0]heptan-6-one-4-carboxylic acid ethyl ester, a novel cyclobutanone analogue of a β-lactam antibiotic is described. This was achieved by [2+2] cycloaddition of a 2,3-dihydrothiophene with dichloroketene, followed by conversion to a cyclobutanol and use of an intramolecular nitrene insertion strategy to install nitrogen functionality at C-7 with endo stereochemistry.
Keywords
?-lactam , Cycloaddition , Ketene , nitrene , Penicillin
Journal title
Tetrahedron
Serial Year
2001
Journal title
Tetrahedron
Record number
1082094
Link To Document