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Issue 16, 1997
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Sulfur-controlled 6-exo aryl radical cyclisation of N-ethenyl-2-(2-bromophenyl)acetamides: synthesis of (±)-tetrahydropalmatine and saulatine

Abstract

Bu3SnH-mediated aryl radical cyclisation of 2-(2-bromophenyl)-N-[2,2-bis(phenylsulfanyl)ethenyl]acetamide 7 takes place in a 6-exo-trig manner to give the isoquinolinone 9. The method has been applied to the synthesis of (±)-tetrahydropalmatine 16 and saulatine 24.

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Article type: Paper
DOI: 10.1039/A702307C
J. Chem. Soc., Perkin Trans. 1, 1997, 2291-2296

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    Sulfur-controlled 6-exo aryl radical cyclisation of N-ethenyl-2-(2-bromophenyl)acetamides: synthesis of (±)-tetrahydropalmatine and saulatine

    H. Ishibashi, H. Kawanami, H. Nakagawa and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1997, 2291
    DOI: 10.1039/A702307C

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