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Synthesis of a novel thiabicyclo[3.2.0]heptan-6-one analogue of penicillin

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. © 2001 Elsevier Science Ltd.
Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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Journal:
TETRAHEDRON
Volume:
57
Issue:
23
Pages:
4999-5007
Publication date:
2001-06-04
DOI:
ISSN:
0040-4020
URN:
uuid:4662de90-cff7-48f2-b827-038ed1613425
Source identifiers:
37862
Local pid:
pubs:37862
Language:
English
Keywords:

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