Synthesis of psoralen analogues based on dibenzofuran

The syntheses of four novel psoralen derivatives, 6a-d, of the benzofurocoumarin (=benzofuro[1]benzopyranone) type containing an ester group are described. These compounds might be of interest in PUVA (psoralen long-wave ultraviolet radiation) therapy. The overall efficiency of the synthetic procedu...

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Bibliographic Details
Main Author: Campos, Ana M. F. Oliveira (author)
Other Authors: Oliveira, Ana M. A. G. (author), Raposo, M. Manuela M. (author), Griffiths, John (author), Machado, António E. H. (author)
Format: article
Language:eng
Published: 2003
Subjects:
Online Access:http://hdl.handle.net/1822/1803
Country:Portugal
Oai:oai:repositorium.sdum.uminho.pt:1822/1803
Description
Summary:The syntheses of four novel psoralen derivatives, 6a-d, of the benzofurocoumarin (=benzofuro[1]benzopyranone) type containing an ester group are described. These compounds might be of interest in PUVA (psoralen long-wave ultraviolet radiation) therapy. The overall efficiency of the synthetic procedure is greatly limited by the low yields for the penultimate step, i.e. formylation of the dibenzofuranols 3a,c or protected dibenzofuranol 4d to the carboxaldehydes 5 (Scheme 4). However, the final stage to form the pyranone ring from 5a-d proceeds smoothly (Scheme 5).