title: Total Synthesis of Clerobungin A via a Cascade Cyclization Reaction.
abstract: The first total synthesis of the novel cyclohexylethanoid natural product clerobungin A has been achieved in six steps and 14% overall yield starting from commercially available tyrosol. Key steps in this sequence include a bioinspired oxidative dearomatization of a phenol and a hemiacetalization/oxa-Michael cascade to form the tricyclic ring system. Resolution of a late-stage intermediate via chiral HPLC allowed for the measurement of the chiroptical properties of both enantiomers of clerobungin A, supporting the scalemic nature of the natural product.
authors.affiliation: Towson University , Department of Chemistry, 8000 York Road, Towson, Maryland 21252, United States.
authors.forename: James
authors.initials: J
authors.lastname: Mease
authors.affiliation: Towson University , Department of Chemistry, 8000 York Road, Towson, Maryland 21252, United States.
authors.forename: Keith P
authors.initials: KP
authors.lastname: Reber
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D003500:Cyclization; D010084:Oxidation-Reduction; D066244:Proton Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
chemical_list: D001688:Biological Products