Utility of Weitz' aminium salt for obtaining quinones as potential synthetic precursors of quassinoids

DOI: 10.1248/cpb.45.613

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 613 - 619 (1997)

Update date:2022-08-02

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Authors:

Takeya, Tetsuya

Motegi, Satoru

Itoh, Toshimasa

Tobinaga, Seisho

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Article abstract of DOI:10.1248/cpb.45.613

Reactions of phenols and phenolic silyl ethers 5, 6, and 7 using Weitz' aminium salt, tris(4-bromophenyl)aminium hexachloroantimonate (BAHA), gave the corresponding quinone derivatives 8, 9, and 10, which may be useful synthons for obtaining quassinoids, the bitter principle of Simaroubaceous plants. Treatment of 10a with silica gel powder resulted in the intramolecular conjugate addition to afford the indanone 11 in good yield.

Full text of DOI:10.1248/cpb.45.613

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