4176-16-3Relevant articles and documents
Total synthesis of valerenic acid
Kopp, Sascha,Schweizer, W. Bernd,Altmann, Karl-Heinz
scheme or table, p. 1769 - 1772 (2009/12/04)
Valerenic acid is a major constituent of valerian root. It exhibits modulatory activity on the GABAA receptor and thus represents a potential new lead structure for the discovery of new anxiolytics. Here we present the enantioselective total sy
Naturally Occurring Terpene Derivatives, 272. On the Constituents of Zexmenia gnaphaloides and the Synthesis of Valerenane Derivatives
Bohlmann, Ferdinand,Lonitz, Michael
, p. 2410 - 2423 (2007/10/02)
The investigation of a Mexican Zexmenia species afforded in addition to known compounds three new eudesmanolides (9-11) as well as five sesquiterpenes (31b, c, 33, 34a, b), the stereochemistry of which could not be established directly.Therefore the main compound 31c has been synthesized.By intramolecular diene synthesis the preparation of a suitable tetrahydroindane (19) was possible.From this, three of the possible four stereoisomeric aldehydes (23c, 24c, 30c) have been prepared.While one of the obtained aldehydes could be transformed into the compound isolated from the Zexmenia species (31c, obtained as ester 31a), the second one yielded valerenal (25c), one of the constituents of Valeriana officinalis.The thermodynamically most stable isomeric aldehyde 24c surprisingly is formed already under very mild conditions from both other aldehydes 23c and 30c.
