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The total synthesis of sevanol, a novel lignan isolated from the thyme plant (Thymus armeniacus)

Author:
Belozerova, O.A., Deigin, V.I., Khrushchev, A.Yu., Dubinnyi, M.A., Kublitski, V.S.
Source:
Tetrahedron 2018 v.74 pp. 1449-1453
ISSN:
0040-4020
Subject:
bioactive properties, chemical structure, dimerization, ferric chloride, lignans, thyme
Abstract:
Recently, a novel lignan sevanol was isolated from the thyme plant Thymus armeniacus. During structure-functional elucidation it showed significant biological activity on ASIC3 acid sensing channels. Herein we describe the first synthesis of sevanol with a 3% overall yield. The construction of a dihydronaphthalene ring by oxidative dimerization of a protected dihydroxycinnamic acid ester in the presence of ferric chloride (III) is a key step in this first total synthesis of sevanol.
Agid:
5922398