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A New Route to Azafluoranthene Natural Products via Direct Arylation.

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.

SUBMITTER: Ponnala S

PROVIDER: S-EPMC3597128 | biostudies-literature | 2013 Feb

REPOSITORIES: biostudies-literature

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A New Route to Azafluoranthene Natural Products via Direct Arylation.

Ponnala Shashikanth S Harding Wayne W WW

European journal of organic chemistry 20130103 6

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 gener ...[more]

PMID: 23503080

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