title: Synthesis of (+/-)-nosyberkol (isotuberculosinol, revised structure of edaxadiene) and (+/-)-tuberculosinol.
abstract: Me(2)AlCl-catalyzed Diels-Alder reaction of N-tigloyloxazolidinone with 6,6-dimethyl-1-vinylcyclohexene selectively provided the exo adduct, which was converted to nosyberkol (isotuberculosinol) and tuberculosinol. The spectral data for nosyberkol are identical with those reported for edaxadiene, whose structure is revised accordingly.
authors.affiliation: Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
authors.forename: Nathan
authors.initials: N
authors.lastname: Maugel
authors.forename: Francis M
authors.initials: FM
authors.lastname: Mann
authors.forename: Matthew L
authors.initials: ML
authors.lastname: Hillwig
authors.forename: Reuben J
authors.initials: RJ
authors.lastname: Peters
authors.forename: Barry B
authors.initials: BB
authors.lastname: Snider
mesh_terms: D002384:Catalysis; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; C547162:edaxadiene; C551415:tuberculosinol
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