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Syntheses of carbocyclic uracil polyoxin C analogs: application of Pd(0)/InI-allylation of 4-acetoxy-2-azetidinone.

ABSTRACT: 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.

SUBMITTER: Cesario C 

PROVIDER: S-EPMC2745051 | biostudies-literature | 2009 Aug

REPOSITORIES: biostudies-literature

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Syntheses of carbocyclic uracil polyoxin C analogs: application of Pd(0)/InI-allylation of 4-acetoxy-2-azetidinone.

Cesario Cara C   Miller Marvin J MJ  

The Journal of organic chemistry 20090801 15

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. ...[more]

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