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Syntheseversuche in der Griseofulvinreihe. 5. Mitteilung. Zur Synthese von (−)‐ und (+)‐Griseofulvin und ihrer Diastereomeren
Author(s) -
Brossi A.,
Baumann M.,
Burkhardt F.
Publication year - 1962
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.19620450427
Subject(s) - chemistry , diastereomer , griseofulvin , stereochemistry , enantiomer , dermatology , medicine
Abstract Rac. epigriseofulvic acid (II) has been resolved and (‐)‐ and (+)‐epigriseo‐fulvin (III) have been synthesized. Epimerisation of (‐)‐ and (+)‐III and separation of the diastereomeric mixtures afforded (‐)‐ and (+)‐griseofulvin (I) respectively. The chemotherapeutic activity of (+)‐I in vitro is practically identical with that of the natural antibiotic whereas the activity of its (‐)‐enantiomer is negligible.