Synthesis of (+/-)-nosyberkol (isotuberculosinol, revised structure of edaxadiene) and (+/-)-tuberculosinol.
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.
Maugel
Nathan
N
Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Mann
Francis M
FM
Hillwig
Matthew L
ML
Peters
Reuben J
RJ
Snider
Barry B
BB
D002384:Catalysis; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
D004224:Diterpenes; C547162:edaxadiene; C551415:tuberculosinol
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