Enantioselective total synthesis of (+)-eupenoxide and (+)-phomoxide: revision of structures and assignment of absolute configuration.
[reaction: see text] Stereo- and enantioselective total syntheses of the novel, polyketide natural products ent-eupenoxide and ent-phomoxide have been accomplished from the readily available Diels-Alder adduct of cyclopentadiene and p-benzoquinone. These synthetic studies necessitate the revision of the assigned stereostructures of the natural products and reveal their absolute configuration.
Mehta
Goverdhan
G
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India. gm@orgchem.iisc.ernet.in
Roy
Subhrangsu
S
D016227:Benzoquinones / Q000737:chemistry; D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D013098:Xylariales / Q000737:chemistry
D016227:Benzoquinones; D003517:Cyclopentanes; D006574:Heterocyclic Compounds, 2-Ring; D007202:Indicators and Reagents; D018942:Macrolides; C495647:phomoxide; C495645:eupenoxide