A General Synthesis of (±)-Dibenzocyclooctadiene Lignans

Tetsuya TAKEYA; Shinobu YAMAKI; Toshimasa ITOH; Hiroko HOSOGAI; Seisho TOBINAGA

doi:10.1248/cpb.44.909

Tetsuya TAKEYA, Shinobu YAMAKI, Toshimasa ITOH, Hiroko HOSOGAI, Seisho TOBINAGA

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Keywords: general synthesis, lignan, dibenzocyclooctadiene, spirodienone ether, Weitz' aminium salt, oxidative aryl-aryl coupling

JOURNAL FREE ACCESS

1996 Volume 44 Issue 5 Pages 909-918

DOI https://doi.org/10.1248/cpb.44.909

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Abstract

We have established a new general synthesis for (±)-dibenzocyclooctadiene lignans, including (±)-schizandrin (1a), (±)-gomisin A (1b), (±)-isoschizandrin (3a), and (±)-isogomisin A (3b), via the spiro-dienone ethers E- and T-11 as the key intermediates, prepared from the corresponding bisarylbutanol derivatives E- and T-10 by the oxidation with Weitz' aminium salt, tris(4-bromophenyl)aminium hexachloroantimonate (BAHA). These syntheses consist of 13 steps from the phenylpropanone 5.

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