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Eine stereospezifische, licht‐ und säurekatalysierte Allylumlagerung; Synthese von Paliclavin. 80. Mitteilung über Mutterkornalkaloide
Author(s) -
Fehr Theo,
Stadler Paul Albert
Publication year - 1975
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.19750580828
Subject(s) - chemistry , stereospecificity , allylic rearrangement , stereochemistry , demethylation , stereoselectivity , metabolite , catalysis , organic chemistry , biochemistry , gene expression , dna methylation , gene
A Stereospecific, Light‐ and Acid Catalyzed Allylic Rearrangement; Syntsesis of Paliclavine The synthesis of paliclavine, a recently isolated metabolite of strain of Claviceps paspali STEVENS et HALL, was achieved by an acid‐ and photo‐sensitized stereoselective allylic rearrangement of chanoclavine‐I and isochanoclavine‐I. In a second approach N‐methyl‐chanoclavine‐I was converted to N‐methyl‐paliclavine by the same method, subsequent N‐demethylation led to paliclavine. The chemical prerequisites and the mechanism of the reaction are discussed.