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Synthesis of (+/-)-nosyberkol (isotuberculosinol, revised structure of edaxadiene) and (+/-)-tuberculosinol
Journal article   Open access   Peer reviewed

Synthesis of (+/-)-nosyberkol (isotuberculosinol, revised structure of edaxadiene) and (+/-)-tuberculosinol

Nathan Maugel, Francis M Mann, Matthew L Hillwig, Reuben J Peters and Barry B Snider
Organic letters, Vol.12(11), pp.2626-2629
06/04/2010
DOI: https://doi.org/10.1021/ol100832h
PMCID: PMC2880386
PMID: 20462237

Abstract

Nuclear Magnetic Resonance, Biomolecular Molecular Structure Catalysis Stereoisomerism Diterpenes - chemical synthesis Diterpenes - chemistry
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.
url
https://doi.org/10.1021/ol100832hView
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