TY - JOUR
T1 - Acid Rearrangement of Secoiridoids Related to Oleuropein and Secologanin
AU - Bianco, Armandodoriano
AU - Jensen, Søren Rosendal
AU - Olesen, Jens
AU - Passacantilli, Pietro
AU - Ramunno, Alessia
PY - 2003
Y1 - 2003
N2 - 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.
AB - 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.
M3 - Journal article
SN - 1434-193X
SP - 4349
EP - 4354
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 22
ER -