Synthesis of (-)-matairesinol, (-)-enterolactone, and (-)-enterodiol from the natural lignan hydroxymatairesinol.
[reaction: see text] We describe here a four-step semisynthetic method for the preparation of enantiomerically pure (-)-enterolactone starting from the readily available lignan hydroxymatairesinol from Norway spruce (Picea abies). Hydroxymatairesinol was first hydrogenated to matairesinol. Matairesinol was esterified to afford the matairesinyl 4,4'-bistriflate, which was deoxygenated by palladium-catalyzed reduction to 3,3'-dimethylenterolactone. Demethylation of 3,3'-dimethylenterolactone and reduction with LiAlH(4) yielded (-)-enterolactone and (-)-enterodiol, respectively.
Eklund
Patrik
P
Department of Organic Chemistry, Abo Akademi University, Biskopsgatan 8, 20500-FIN, Abo, Finland. paeklund@abo.fi
Lindholm
Anna
A
Mikkola
J-P
JP
Smeds
Annika
A
Lehtilä
Reko
R
Sjöholm
Rainer
R
D015107:4-Butyrolactone / Q000031:analogs & derivatives*; D005663:Furans; D006865:Hydrogenation; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D028222:Picea / Q000737:chemistry; D013237:Stereoisomerism
D005663:Furans; D017705:Lignans; C419306:hydroxymatairesinol; C068935:matairesinol; C029498:2,3-bis(3'-hydroxybenzyl)butane-1,4-diol; D015107:4-Butyrolactone; C029497:2,3-bis(3'-hydroxybenzyl)butyrolactone