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Total synthesis of clavulanic acid analogues via isomerisation of 7-oxo-4-oxa-1-azabicyclo[3.2.0]hept-2-enes

✍ Scribed by Bentley, Peter H.; Brooks, Gerald; Gilpin, Martin L.; Hunt, Eric


Book ID
120887807
Publisher
The Royal Society of Chemistry
Year
1977
Tongue
English
Weight
165 KB
Volume
24
Category
Article
ISSN
0022-4936

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Synthesis of some 4-acyloxy-7-oxo-1-azab
✍ John H. Bateson; Alison M. Quinn; Robert Southgate πŸ“‚ Article πŸ“… 1987 πŸ› Elsevier Science 🌐 French βš– 188 KB

Allylic oxidation of 4-allyl-1-dimethyl-t-butylsilylazetidin-2ones (5,7) gave the 4-(l-hydroxyprop-2-ene-1-yl) derivatives (6,8). Radical benzoyloxylation of the silylated 8-oxo-7-azabicyclo[4.2.O]oct-3ene (18) provided four allylic monobenzoates. Progression of ( ) and ( ) afforded, respectively,