A unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins

Tsukasa Hirokane, Yasuaki Hirata, Takayuki Ishimoto, Kentaro Nishii and Hidetoshi Yamada ()
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Tsukasa Hirokane: School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen
Yasuaki Hirata: School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen
Takayuki Ishimoto: School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen
Kentaro Nishii: School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen
Hidetoshi Yamada: School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen

Nature Communications, 2014, vol. 5, issue 1, 1-10

Abstract: Abstract Ellagitannins are a family of polyphenols containing more than 1,000 natural products. Nearly 40% of these compounds contain a highly oxygenated diaryl ether that is one of the most critical elements to their structural diversity. Here, we report a unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins. The strategy involves oxa-Michael addition of phenols to an orthoquinone building block, with subsequent elimination and reductive aromatization. The design of the building block—a halogenated orthoquinone monoketal of gallal—reduces the usual instability of orthoquinone and controls addition/elimination. Reductive aromatization is achieved with perfect chemoselectivity in the presence of other reducible functional groups. This strategy enables the synthesis of different diaryl ethers. The first total synthesis of a natural ellagitannin bearing a diaryl ethers is performed to demonstrate that the strategy increases the number of synthetically available ellagitannins.

Date: 2014
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DOI: 10.1038/ncomms4478

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