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Synthesis 2011(9): 1456-1464
DOI: 10.1055/s-0030-1259982
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
Further Information
Publication History
Received
24 January 2011
Publication Date:
01 April 2011 (online)


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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