Synthesis of trisphaeridine and norchelerythrine through palladium-catalyzed aryl-aryl coupling reactions

Takashi Harayama, Hisashi Akamatsu, Kana Okamura, Taeko Miyagoe, Toshihiko Akiyama, Hitoshi Abe, Yasuo Takeuchi

Research output: Contribution to journalArticle

100 Citations (Scopus)

Abstract

The synthesis of triphaeridine and norchelerythrine through palladium-catalyzed aryl-aryl coupling reactions was studied. The secondary amides were synthesized from 6-bromopiperonylicacid and aniline, and from piperonylic acid and 2-iodoaniline respectively, and were methoxymethylated for the preparation of starting materials for the cyclization reaction. All experiments were carried out in an argon atmosphere and the extract was washed with brine. The nuclear magnetic resonance (NMR) spectral data showed the presence of singlet signals due to aromatic proton in the products.

Original languageEnglish
Pages (from-to)523-528
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number5
Publication statusPublished - Mar 7 2001

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Argon
Cyclization
Palladium
Amides
Protons
Nuclear magnetic resonance
Experiments
chelerythrine
trispheridine
brine
aniline
piperonylic acid
2-iodobenzenamine

ASJC Scopus subject areas

  • Chemistry(all)

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Synthesis of trisphaeridine and norchelerythrine through palladium-catalyzed aryl-aryl coupling reactions. / Harayama, Takashi; Akamatsu, Hisashi; Okamura, Kana; Miyagoe, Taeko; Akiyama, Toshihiko; Abe, Hitoshi; Takeuchi, Yasuo.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 5, 07.03.2001, p. 523-528.

Research output: Contribution to journalArticle

Harayama, Takashi ; Akamatsu, Hisashi ; Okamura, Kana ; Miyagoe, Taeko ; Akiyama, Toshihiko ; Abe, Hitoshi ; Takeuchi, Yasuo. / Synthesis of trisphaeridine and norchelerythrine through palladium-catalyzed aryl-aryl coupling reactions. In: Journal of the Chemical Society, Perkin Transactions 1. 2001 ; No. 5. pp. 523-528.
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AU - Abe, Hitoshi

AU - Takeuchi, Yasuo

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