Reactions of the natural lignan hydroxymatairesinol in basic and acidic nucleophilic media: formation and reactivity of a quinone methide intermediate.
The chemical properties and synthetic modifications of the natural lignan hydroxymatairesinol in basic and acidic nucleophilic media were studied. Hydroxymatairesinol presumably reacts via a quinone methide and a carbonium ion mechanism under basic and acidic conditions, respectively. In these conditions the benzylic hydroxyl group was displaced by nucleophiles yielding new 7-substituted butyrolactone lignans. Reactions in alcoholic basic solutions yielded the 7-alkoxy ethers diastereoselectively. Several previously known lignans as well as new lignans and lignan derivatives were synthesised. The transformations were monitored and the products identified by HPLC-MS and NMR.
Eklund
Patrik C
PC
Process Chemistry Centre, Department of Organic Chemistry, Abo Akademi University, Piispankatu 8, 20500-FIN, Turku, Finland. paeklund@abo.fi
Sundell
Fredrik J
FJ
Smeds
Annika I
AI
Sjoholm
Rainer E
RE