Synthesis of (−)-Matairesinol, (−)-Enterolactone, and (−)-Enterodiol from the Natural Lignan Hydroxymatairesinol
- 18 January 2003
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (4) , 491-493
- https://doi.org/10.1021/ol0273598
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.Keywords
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