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Synthesis 2011(9): 1456-1464  
DOI: 10.1055/s-0030-1259982
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Access to Chiral β-Benzyl-γ-butyrolactones and Its Application to the Synthesis of Enantiopure (+)-Secoisolariciresinol, (-)-Secoisolariciresinol, and (-)-Enterolactone

Florent Allais*, Thomas J. L. Pla, Paul-Henri Ducrot*
INRA/AgroParisTech UMR1318 Institut Jean-Pierre Bourgin, INRA route de Saint-Cyr, 78026 Versailles Cedex, France
Fax: +33(1)30833119; e-Mail: florent.allais@versailles.inra.fr;
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Publication History

Received 24 January 2011
Publication Date:
01 April 2011 (online)

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Abstract

Both enantiomers of secoisolariciresinol and enantiopure (-)-enterolactone were synthesized through a highly stereoselective convergent synthesis. An Evans diastereoselective alkylation followed by a substrate-induced diastereoselective α-alkylation of the newly formed optically active β-benzyl-γ-butyrolactone gave the β-β′ linkage of the target skeleton. The (S,S)- and (R,R)-enantiomers of secoisolariciresinol and (-)-enterolactone were obtained in 12-14% (11 steps) and 20% (7 steps) overall yield, respectively.

Key words

total synthesis - natural product - lactones - asymmetry - diastereoselective alkylation

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