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

作者：Allais Florent^*; Pla Thomas J L; Ducrot Paul Henri

来源：Synthesis (Germany), 2011, 2011(9): 1456-1464.

DOI：10.1055/s-0030-1259982

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

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 alpha-alkylation of the newly formed optically active beta-benzyl-gamma-butyrolactone gave the beta-beta' 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.

• 出版日期2011-5