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Synthesis 2010(12): 2023-2026  
DOI: 10.1055/s-0029-1218744
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of a Cyclopent[g]isoquinoline Building Block for Fredericamycin A

Manfred Braun*a, Gwenaëlle Kergoëta, Fabian Kruskaa, Walter Frankb
a Institut für Organische Chemie und Makromolekulare Chemie, Universität Düsseldorf, 40225 Düsseldorf, Germany
Fax: +49(211)8115079; e-Mail: braunm@uni-duesseldorf.de;
b Institut für Anorganische Chemie und Strukturchemie, Universität Düsseldorf, 40225 Düsseldorf, Germany
Further Information

Publication History

Received 6 January 2010
Publication Date:
15 April 2010 (online)

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Abstract

A new route to the DEF-ring building block of fredericamycin A has been elaborated. The five-step synthesis involves a photo-Wolff reaction as the key step and leads to carboxylic acid 2 in 27% overall yield, starting from the pyridine derivative 3. Two intermediates, the tricyclic ketones 6a and 7, are characterized by crystal structure analyses.

Key words

heterocycles - rearrangement - diazo compounds - annulation - carboxylic acids

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Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 758035 (6a) and CCDC 758036 (7). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].