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Die Struktur des Antibioticums Roridin H. Verrucarine und Roridine, 20. Mitt. [1]
Author(s) -
Traxler P.,
Tamm Ch.
Publication year - 1970
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.19700530733
Subject(s) - chemistry , stereochemistry , acetaldehyde , hydrolysis , acetal , adipic acid , medicinal chemistry , organic chemistry , ethanol
Structure 1 has been established for roridin H (C 29 H 36 O 8 ), an antibiotic isolated from Myrothecium verrucaria and formerly namend verrucarin H [3]. Base catalysed hydrolysis of 1 gave the known terpene alcohol verrucarol ( 8 ; C 15 H 22 O 4 ) and myrothecinic acid ( 3 ; C 14 H 18 O 6 ), a previously undescribed dicarboxylic acid. The structure of 3 was determined by spectral methods and by chemical cleavage of the unusual acetal group of dimethyl hexahydromyrothecinoate ( 6 ) by hydrolysis with HCl in the presence of 2, 4‐dinitrophenylhydrazine, producing the 2, 4‐dinitrophenylhydrazone 13 of 3‐methylglutaric acid semialdehyde 10 and methyl 6, 7‐dihydroxy‐octanoate ( 11 ). 13 was transformed in to dimethyl 3‐methylglutarate ( 15 ). Cleavage of 11 with HIO 4 gave acetaldehyde and adipic acid semialdehyde ( 17 ) which was oxidized to adipic acid ( 19 ). The 220 MHz NMR spectra of roridin H ( 1 ) and dimethyl hexahydromyrothecinoate ( 6 ) allowed unequivocal assignment of the signals to the majority of the protons in the antibiotic.