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Über die Verrucarine und Roridine. 2. (vorläufige) Mitteilung. Partialstruktur von Verrucarin A
Author(s) -
Tamm Ch.,
Gutzwiller J.
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.19620450539
Subject(s) - chemistry , muconic acid , bicyclic molecule , stereochemistry , hydrolysis , sesquiterpene , lactone , absolute configuration , acid hydrolysis , organic chemistry , benzene
The base catalysed hydrolysis of the antibiotic verrucarin A (C 27 H 34 O 9 ) yields three products: (1) verrucarol (C 15 H 22 O 4 ), a new sesquiterpene which is probably bicyclic, (2) muconic acid (C 6 H 6 O 4 ), a new sesquiterpene which is probably bicyclic, (2) muconic acid (C 6 H 6 O 4 ; cis , cis or cis , trans ) and (3) verrucarinolactone (C 6 H 10 O 3 ), the δ‐lactone of the hitherto unknown trans‐α,δ‐dihydroxy‐β‐methylvaleric acid. The absolute configuration of verrucarinolactone is deduced by its correlation with (R)‐(+)‐methylsuccinic acid. Verrucarinic acid represents a new natural isomer of mevalonic acid.