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

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

References

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13

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: [phone] or e-mail: [e-mail]].