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Synthesis of Psoralen Analogues Based on Dibenzofuran
Author(s) -
Oliveira Ana M. A. G.,
Raposo M. Manuela M.,
OliveiraCampos Ana M. F.,
Griffiths John,
Machado Antonio E. H.
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390237
Subject(s) - psoralen , chemistry , dibenzofuran , formylation , ring (chemistry) , ultraviolet , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , dna , catalysis , quantum mechanics , physics
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 ).