Synthesis of (±)-Nosyberkol (Isotuberculosinol, Revised Structure of Edaxadiene) and (±)-Tuberculosinol
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2010-01-01
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Peters, Reuben
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Biochemistry, Biophysics and Molecular Biology
Abstract
Me2AlCl-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.
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Reprinted with permission from Organic Letters 12 (2010): 2626, doi:10.1021/ol100832h. Copyright (2010) American Chemical Society.
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Fri Jan 01 00:00:00 UTC 2010