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Carbocyclic uracil polyoxin C analogs are prepared from an acylnitroso-derived hetero Diels-Alder cycloadduct in fewer than nine steps. Pd(0)/InI-mediated allylation of 4-acetoxy-2-azetidinone is used to install the beta-amino acid side chain at the C-5' position of the carbocycle.

journal of organic chemistry

Syntheses of Carbocyclic Uracil Polyoxin C Analogs: Application of Pd(0)/InI-Allylation of 4-Acetoxy-2-azetidinone†We dedicate this paper to Professor Jeremiah P. Freeman on the occasion of his 80th birthday and with thanks for his outstanding service to the profession of organic chemistry through his 25 years as secretary of Organic Syntheses.