Asymmetric Synthesis of Iridoid Derivatives Using Resolved 2-Phenylindoline as a Chiral Auxiliary

被引：8

作者：

Santangelo, Ellen M. ^{[1
,2
]}

Liblikas, Ilme ^{[3
]}

Mudalige, Anoma ^{[2
]}

Tornroos, Karl W. ^{[4
]}

Norrby, Per-Ola ^{[5
]}

Unelius, C. Rikard ^{[1
]}

机构：

[1] Univ Kalmar, Sch Pure & Appl Nat Sci, S-39182 Kalmar, Sweden

[2] Royal Inst Technol, Dept Organ Chem, KTH Chem Sci & Engn, S-10044 Stockholm, Sweden

[3] Univ Tartu, Inst Technol, EE-50411 Tartu, Estonia

[4] Univ Bergen, Dept Chem, N-5007 Bergen, Norway

[5] Univ Gothenburg, Dept Chem, S-41296 Gothenburg, Sweden

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 35期

关键词：

Iridoid; Cycloaddition reaction; Nepetalactol; Chromatographic resolution; 2-Phenylindoline;

D O I：

10.1002/ejoc.200800440

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric synthetic route to cis,cis-nepetalactol (component of the sex pheromone for the hop aphid, Phorodon humuli) is presented. 2-Phenylindoline was resolved to provide a chiral auxiliary for the cycloaddition of oxocitral. The resolution was made by chromatographic separation of the diastereomers of the urea derivative made from 2-phenylindoline and with (R)-(+)-alpha-methylbenzyl isocyanate, followed by reductive cleavage of the isolated diasteromers using diborane. The cycloaddition of oxocitral using (S)-2-phenylindoline yielded an enantiopure product after chromatography. Hydrolysis of the cycloaddition adduct yielded gastrolactol (3). As gastrolactol is a versatile synthon for the synthesis of iridoids, the overall procedure provides a general asymmetric route to elaborated iridoids. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：5915 / 5921

页数：7

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