Synthesis of (-)-Matairesinol, (-)-Enterolactone, and (-)-Enterodiol from the Natural Lignan Hydroxymatairesinol

A1 Originalartikel i en vetenskaplig tidskrift (referentgranskad)


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Publikationens författare: Patrik Eklund, Anna Lindholm, J.-P. Mikkola, Annika Smeds, Reko Lehtilä, and R. Sjöholm
Förläggare: AMER CHEMICAL SOC
Publiceringsår: 2003
Tidskrift: Organic Letters
Tidskriftsakronym: ORG LETT
Volym: 5
Nummer: 4
Artikelns första sida, sidnummer: 491
Artikelns sista sida, sidnummer: 493
Antal sidor: 3
ISSN: 1523-7060


Abstrakt

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 LiAlH4 yielded (-)-enterolactone and (-)-enterodiol, respectively.

Senast uppdaterad 2019-21-10 vid 03:07