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Synthesis of 1-methoxy canthine-6-one

✍ Scribed by Timothy J. Hagen; James M. Cook

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
221 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

The six step synthesis of the cytotoxic antileukemic alkaloid 1-methoxy canthine-&one 2 is described.

The pivotal steps m represented by the oxidation (DDQ) of 9 to tiord the 3-acylindole 14 and the conversion of 11 into the 4-methoxy-1-alkyl fl-carboline 15.

A number of canthine-6-one alkaloids have been isolated recently from various plants. Among these are

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An Improved Synthesis of Canthin-6-one.
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✍ Ulrich Rößler; Siegfried Blechert; Eberhard Steckhan 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 175 KB

The cytotoxic alkaloid canthin-6-one was synthesized from harmalane in a short sequence (six steps) with good overall yield (18%) using a single electron transfer (SET) induced radical cationic hetero [4+2] cycloaddition as high yielding key step.