A Convenient New Route to 4-Substituted Benzo[de][3,6]Phenanthrolin-6(6H)-Ones: Important Intermediates in the Synthesis of Ring-A Analogues of the Cytotoxic Marine Alkaloid Ascididemin

Brent R. Copp Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand

Richard P. Hansen Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand

David R. Appleton Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand

Brent S. Lindsay Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand

Chris J. Squire Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand

George R. Clark Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand

Cliff E. F. Rickard Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand

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Abstract

4-ethylthio- and 4-(4″-methylphenylthio)benzo[de][3,6]phenanthrolin-6(6H)-one have been synthesised in 4 steps from benzoquinone and then readily converted to the 4-amino (6d) and 4-methoxy (6c) analogues by nucleophilic substitution. Further elaboration of 6d leads to the synthesis of 11-hydroxyascididemin, which we have found to exhibit antiviral activity in vitro.

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A Convenient New Route to 4-Substituted Benzo[de][3,6]Phenanthrolin-6(6H)-Ones: Important Intermediates in the Synthesis of Ring-A Analogues of the Cytotoxic Marine Alkaloid Ascididemin

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A Convenient New Route to 4-Substituted Benzo[de][3,6]Phenanthrolin-6(6H)-Ones: Important Intermediates in the Synthesis of Ring-A Analogues of the Cytotoxic Marine Alkaloid Ascididemin

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