A general synthesis of (±)-dibenzocyclooctadiene lignans

DOI: 10.1248/cpb.44.909

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 909 - 918 (1996)

Update date:2022-08-04

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Authors:

Takeya, Tetsuya

Yamaki, Shinobu

Itoh, Toshimasa

Hosogai, Hiroko

Tobinaga, Seisho

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Article abstract of DOI:10.1248/cpb.44.909

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.

Full text of DOI:10.1248/cpb.44.909

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