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

Patrik Christoffer Eklund; Anna Lindholm; Jyri-Pekka Mikkola; Annika Smeds; Reko Lehtilä; Rainer Sjöholm

doi:10.1021/ol0273598

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

Patrik Christoffer Eklund, Anna Lindholm, Jyri-Pekka Mikkola, Annika Smeds, Reko Lehtilä, Rainer Sjöholm

Research output: Contribution to journal › Article › Scientific › peer-review

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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.

Original language	Undefined/Unknown
Pages (from-to)	491–493
Number of pages	3
Journal	Organic Letters
Volume	5
Issue number	4
DOIs	https://doi.org/10.1021/ol0273598
Publication status	Published - 2003
MoE publication type	A1 Journal article-refereed

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10.1021/ol0273598

Cite this

@article{e83ee9f4352e43a58e28c19162e38a1e,

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

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.",

author = "Eklund, \{Patrik Christoffer\} and Anna Lindholm and Jyri-Pekka Mikkola and Annika Smeds and Reko Lehtil{\"a} and Rainer Sj{\"o}holm",

year = "2003",

doi = "10.1021/ol0273598",

language = "Odefinierat/ok{\"a}nt",

volume = "5",

pages = "491–493",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "4",

}

TY - JOUR

T1 - Synthesis of (-)-Matairesinol, (-)-Enterolactone, and (-)-Enterodiol from the Natural Lignan Hydroxymatairesinol

AU - Eklund, Patrik Christoffer

AU - Lindholm, Anna

AU - Mikkola, Jyri-Pekka

AU - Smeds, Annika

AU - Lehtilä, Reko

AU - Sjöholm, Rainer

PY - 2003

Y1 - 2003

N2 - 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.

AB - 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.

U2 - 10.1021/ol0273598

DO - 10.1021/ol0273598

M3 - Artikel

SN - 1523-7060

VL - 5

SP - 491

EP - 493

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -