Use of an Iodonium Ylide in the Synthesis of p-Nitrobenzyl (6R,7S) 3-Hydroxy-8-oxo-7-phenoxyacetamido-1-azabicyclo [4.2.0]octa-2-ene-2-carboxylate. -The title compound (IV), a key intermediate in the synthesis of carbacephalosporins, is prepared by Rh(II)-catalyzed cyclization of the iodonium ylide
Use of an iodonium ylide in the synthesis of p-nitrobenzyl (6R, 7S) 3-hydroxy-8-oxo-7-phenoxyacetamino-1-azabicyclo[4.2.0]octa-2-ene-2-carboxylate
β Scribed by Radhe K. Vaid; Thomas E. Hopkins
- Book ID
- 104257986
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 197 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
p-Nitrobenzyl (61L7S)-3-hydroxy-8-oxo-7-phenoxyacetamido-l-azabicyclo [4.2.0]octa-2-ene-2-carboxyate (6) was synthesized utilizing rhodium(II)-or acid-catalyzed cyclization of iodonium ylide (5). The iodonium ylide (5) was easily prepared from the corresponding 13-keto ester (4) and [(diacetoxy)iodo]benzene in good yield.
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The synthesis of the title compound (4) is described. ## Treatment of (3S)-[(lR)-hydroxyethyl]-(4R)- [ 3-(p-nitrobenzyloxy) carbonyl-2-0x0-[ 2-I4C] -3-diazopropan-l-yl]azetidin-2-one1 with rhodium diacetate achieved ring closure forming (5R,6S)-pnitrobenzyl-6-~(1R)-hydroxyethyl]-3,7-dioxo-[3-14C]
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