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A New Route to Azafluoranthene Natural Products via Direct Arylation
Shashikanth Ponnala1, Wayne W Harding
1Chemistry Department, Hunter College, City University of New York, 695 Park Avenue, NY 10065, USA.
Abstract:
Microwave-assisted direct arylation was successfully employed in the synthesis of azafluoranthene alkaloids for the first time. Direct arylation reactions on a diverse set of phenyltetrahydroisoquinolines produces the indeno[1,2,3-ij]isoquinoline nucleus en route to a high yielding azafluoranthene synthesis. The method was used as a key step in the efficient preparation of the natural products rufescine and triclisine. As demonstrated herein, this synthetic approach should be generally applicable to the preparation of natural and un-natural azafluoranthene alkaloids as well as "azafluoranthene-like" isoquinoline alkaloids.
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