Asymmetric synthesis of the fully elaborated pyrrolidinone core of oxazolomycin A.

Journal article

The asymmetric synthesis of the key pyrrolidinone core, including a highly elaborated exocyclic carbon chain, of the γ-lactam β-lactone antibiotic oxazolomycin A is described. Principal features include the Birch reduction of an aromatic pyrrole nucleus, a late stage RuO(4) catalyzed pyrrolidine oxidation, and a highly diastereoselective organocerium addition to an aldehyde.

Authors: Donohoe, T; O'Riordan, T; Peifer, M; Jones, C; Miles, T

• Publication status: Published
• Journal: Organic letters
• Volume: 14
• Issue: 21
• Pages: 5460-5463
• Publication date: 2012-11-01
• DOI: 10.1021/ol302541j
• EISSN: 1523-7052
• ISSN: 1523-7060
• Language: English
• Keywords: Streptomyces; Catalysis; Pyrrolidinones; Spiro Compounds; Oxidation-Reduction; Stereoisomerism; Ruthenium Compounds; Oxazoles; Molecular Structure