Synthesis of (±)-Nosyberkol (Isotuberculosinol, Revised Structure of Edaxadiene) and (±)-Tuberculosinol

被引：29

作者：

Maugel, Nathan ^{[1
]}

Mann, Francis M. ^{[2
]}

Hillwig, Matthew L. ^{[2
]}

Peters, Reuben J. ^{[2
]}

Snider, Barry B. ^{[1
]}

机构：

[1] Brandeis Univ, Dept Chem MS 015, Waltham, MA 02454 USA

[2] Iowa State Univ, Dept Biochem Biophys & Mol Biol, Ames, IA 50011 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 11期

基金：

美国国家卫生研究院;

关键词：

DITERPENE CYCLASE; TUBERCULOSIS; DERIVATIVES; DYSIDIOLIDE; ACIDS;

D O I：

10.1021/ol100832h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2626 / 2629

页数：4

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