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SnCl4-mediated oxidative reaction for formation of binaphthoquinone and dinaphthofuran frameworks and its application to natural product synthesis

✍ Scribed by Tokutaro Ogata; Iwao Okamoto; Hirohisa Doi; Eiichi Kotani; Tetsuya Takeya

Book ID
104253128
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
293 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

A simple method was developed for the direct synthesis of 2,2%-binaphthoquinones and dinaphtho[1,2-b;2%,1%-d]furans, utilizing an oxidative reaction via electron donor-acceptor complexes of 1-naphthols with SnCl 4 in the absence or presence of dioxygen. As an application of this method to natural product synthesis, we describe a facile biomimetic synthesis of several binaphthoquinones, 3,3%-bijuglone, 3,3%-biplumbagin and elliptinone.

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The aryl–aryl coupling reaction of 1-nap
The aryl–aryl coupling reaction of 1-naphthol with SnCl4 for 2,2β€²-binaphthol synthesis and its application to the biomimetic synthesis of binaphthoquinone isolated from Plumbago zeylanica
✍ Iwao Okamoto; Hirohisa Doi; Eiichi Kotani; Tetsuya Takeya πŸ“‚ Article πŸ“… 2001 πŸ› Elsevier Science 🌐 French βš– 71 KB

A simple method for the direct synthesis of 2,2%-binaphthols was developed, utilizing aryl-aryl coupling reaction via electron donor-acceptor complexes of 1-naphthols with SnCl 4 . Heating of the complex in a sealed tube afforded the corresponding o-o coupling product in excellent yield. This method