Revidierte Struktur von Verrucarin E. Eine Synthese des Antibioticums und verwandter β‐Acetyl‐Pyrrol‐Derivate. Verrucarine und Roridine, 18. Mitteilung [1]

• Published in: Helvetica Chimica Acta
• Main Authors: Pfäffli, P., Tamm, Ch.
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 1969
• Subjects: Carbonic acid
• Online Access: http://dx.doi.org/10.1002/hlca.19690520716; http://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fhlca.19690520716; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fhlca.19690520716; https://onlinelibrary.wiley.com/doi/pdf/10.1002/hlca.19690520716

Abstract The structure of Verrucarin E, an antibiotic isolated from Myrothecium verrucaria , has been corrected (cf. [4]) and shown to be that of 3‐acetyl‐4‐hydroxymethyl‐pyrrole ( 2 ) by comparison with a variety of β‐acetylpyrrole‐derivatives, whose NMR. chemical shifts and coupling constants are reported. Verrucarin E ( 2 ) has been synthesized in low yield from 3‐acetylpyrrole ( 12 ). The following previously unknown β‐acetylpyrrole‐derivatives are described: 3‐acetyl‐5‐methyl‐pyrrole‐2‐carbonic‐acid ( 11 ), 4‐acetyl‐2‐methyl‐pyrrole ( 13 ), 3‐acetyl‐4‐formyl‐pyrrole ( 7 ), 3‐acetyl‐1‐hydroxymethyl‐pyrrole ( 14 ), 3‐(3‐hydroxypropionyl)‐pyrrole ( 15 ), 3‐(3‐hydroxy‐2‐hydroxymethyl‐propionyl)‐pyrrole ( 16 ), and 3‐(3‐acetyl‐pyrr‐1‐yl)‐1‐(pyrr‐3‐yl)‐propan‐1‐one ( 17 ).