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Acid Rearrangement of Secoiridoids Related to Oleuropein and Secologanin
Author(s) -
Bianco Armandodoriano,
Jensen Soren Rosendal,
Olesen Jens,
Passacantilli Pietro,
Ramunno Alessia
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300348
Subject(s) - chemistry , enol , enol ether , stereochemistry , organic chemistry , acetal , hydrolysis , conjugated system , catalysis , polymer
Acid treatment of an iridoid glycoside results in the cleavage of the acetal bond between the sugar unit and the monoterpenoid aglycon. Iridoids possessing non‐conjugated enol ether systems, however, undergo the hydration of the iridoid enol ether functionality in acid medium, as well as the hydrolysis of the bond. We examined the acid rearrangement of secoiridoids such as oleuropein ( 1 ) and secologanin ( 2 ) and their reduction products oleuropeinol ( 3 ) and secologaninol ( 4 ), to examine whether similar behaviour also occurs in this case. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)