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

A1 Journal article (refereed)


Internal Authors/Editors


Publication Details

List of Authors: Patrik Eklund, Anna Lindholm, J.-P. Mikkola, Annika Smeds, Reko Lehtilä, and R. Sjöholm
Publisher: AMER CHEMICAL SOC
Publication year: 2003
Journal: Organic Letters
Journal acronym: ORG LETT
Volume number: 5
Issue number: 4
Start page: 491
End page: 493
Number of pages: 3
ISSN: 1523-7060


Abstract

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.

Last updated on 2019-22-07 at 05:09