Asymmetric synthesis of the fully elaborated pyrrolidinone core of oxazolomycin A.
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.
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK. timothy.donohoe@chem.ox.ac.uk
Timothy J
TJ
Donohoe
Timothy J C
TJ
O'Riordan
Manuel
M
Peifer
Christopher R
CR
Jones
Timothy J
TJ
Miles
D002384:Catalysis; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D017975:Ruthenium Compounds / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D010080:Oxazoles; D011760:Pyrrolidinones; D017975:Ruthenium Compounds; D013141:Spiro Compounds; C077919:diffusomycin; C027646:ruthenium tetraoxide