title: Synthesis of (-)-matairesinol, (-)-enterolactone, and (-)-enterodiol from the natural lignan hydroxymatairesinol.
abstract: [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.
authors.affiliation: Department of Organic Chemistry, Abo Akademi University, Biskopsgatan 8, 20500-FIN, Abo, Finland. paeklund@abo.fi
authors.forename: Patrik
authors.initials: P
authors.lastname: Eklund
authors.forename: Anna
authors.initials: A
authors.lastname: Lindholm
authors.forename: J-P
authors.initials: JP
authors.lastname: Mikkola
authors.forename: Annika
authors.initials: A
authors.lastname: Smeds
authors.forename: Reko
authors.initials: R
authors.lastname: Lehtilä
authors.forename: Rainer
authors.initials: R
authors.lastname: Sjöholm
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives*; D005663:Furans; D006865:Hydrogenation; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D028222:Picea / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: 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