Studies on Natural p-Terphenyls: Total Syntheses of Vialinin A and Terrestrin B

Yue Qi YE; Hiroyuki KOSHINO; Jun-ichi ONOSE; Kunie YOSHIKAWA; Naoki ABE; Shunya TAKAHASHI

doi:10.1271/bbb.90661

Organic Chemistry Regular Papers

Studies on Natural p-Terphenyls: Total Syntheses of Vialinin A and Terrestrin B

Yue Qi YE, Hiroyuki KOSHINO, Jun-ichi ONOSE, Kunie YOSHIKAWA, Naoki ABE, Shunya TAKAHASHI

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Keywords: TNF-α, terphenyl, vialinin A, terrestin B, Suzuki-Miyaura coupling

JOURNAL FREE ACCESS

2010 Volume 74 Issue 1 Pages 140-146

DOI https://doi.org/10.1271/bbb.90661

View "Advance Publication" version (January 7, 2010).

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Abstract

A powerful inhibitor of TNF-α production, vialinin A, was synthesized from sesamol through a series of reactions involving double Suzuki-Miyaura coupling, 2,3-dichloro-5,6-dicyano-1,4-benzoquino (DDQ) mediated de-methoxymethylation and oxidative removal of methylene acetal by lead tetraacetate. The synthetic method also made it possible to prepare a related compound, terrestrin B.

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