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Issue 58, 2013
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A tandem Friedel–Crafts based method for the construction of a tricyclic pyrroloquinoline skeleton and its application in the synthesis of ammosamide B

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Abstract

A total synthesis of ammosamide B (2), a member of the pyrroloquinoline alkaloid family isolated from marine Streptomyces, is described. The characteristic core tricyclic structure of 2 was constructed using a novel, tandem Friedel–Crafts reaction sequence to transform the symmetric tetra-amino substituted benzene derivative 7 into the tricyclic pyrroloquinoline product 8, which serves as an important intermediate in the route to the synthesis of the target natural product.

Graphical abstract: A tandem Friedel–Crafts based method for the construction of a tricyclic pyrroloquinoline skeleton and its application in the synthesis of ammosamide B

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Publication details

The article was received on 05 Apr 2013, accepted on 30 May 2013, published on 30 May 2013 and first published online on 30 May 2013


Article type: Communication
DOI: 10.1039/C3CC42463D
Citation: Chem. Commun., 2013,49, 6519-6521
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    A tandem Friedel–Crafts based method for the construction of a tricyclic pyrroloquinoline skeleton and its application in the synthesis of ammosamide B

    Y. Takayama, T. Yamada, S. Tatekabe and K. Nagasawa, Chem. Commun., 2013, 49, 6519
    DOI: 10.1039/C3CC42463D

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