Angewandte Chemie International Edition · 2016 · 41 citations · 51 references
PharmacyMedicinal ChemistryPharmacologyDrug DiscoveryStructural BiologySynthetic Medicinal ChemistryConformational AnalysisRetrosynthetic AnalysisStructure-activity Relationship AnalysisAdverse Effect CharacterizationBiological Evaluation ReportFluorine ChemistryLipophilicity RelationshipsRelative Configuration DeterminationSubstituent Effects On Lipophilicity
We disclose the syntheses of (+)-bromodanicalipin A as well as (±)-fluorodanicalipin A. The relative configuration and ground-state conformation in solution of both molecules was secured by J-based configuration analysis which revealed that these are identical to natural danicalipin A. Furthermore, preliminary toxicological investigations suggest that the adverse effect of danicalipin A may be due to the lipophilicity of the halogens.
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Nobuaki Matsumori, Daisuke Kaneno, Michio Murata et al. · The Journal of Organic Chemistry · 1999 · 769 citations
David A. Evans, Amir H. Hoveyda · Journal of the American Chemical Society · 1990 · 411 citations