通过一锅氧化[3,3]重排/Friedel-Crafts 芳基化反应立体选择性合成四氢萘酮型和萘基型木脂素。
Stereocontrolled syntheses of tetralone- and naphthyl-type lignans by a one-pot oxidative [3,3] rearrangement/Friedel-Crafts arylation.
机构信息
Department of Chemistry, Northwestern University, 2145 Sheridan Rd, Evanston, IL 60208 (USA).
出版信息
Angew Chem Int Ed Engl. 2014 Jan 27;53(5):1395-8. doi: 10.1002/anie.201307659. Epub 2013 Dec 16.
PMID:24356917
Abstract
The development of a stereoselective one-pot oxidative [3,3] sigmatropic rearrangement/Friedel-Crafts arylation that provides enantioenriched benzhydryl compounds is reported. The utility of this new transformation is demonstrated by the concise synthesis of several tetralone- and naphthyl-type lignan natural products, many of which display anti-malarial activity.
摘要
本文报道了一种对映选择性的一锅氧化[3,3]σ重排/Friedel-Crafts 芳基化反应，该反应提供了对映富集的苯甲酰基化合物。通过简洁合成几种四氢酮和萘基型木脂素天然产物，证明了这种新转化的实用性，其中许多产物具有抗疟活性。
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