Simple Synthesis of trans-.ALPHA.,.BETA.-Dibenzyl-.GAMMA.-butyrolactone Lignans by Diastereoselective Reduction of .ALPHA.-Benzylidene-.BETA.-benzyl-.GAMMA.-butyrolactones Using NaBH4-NiCl2.

trans-α,β-Dibenzyl-γ-butyrolactone lignans were synthesized by stereoselective reduction of α-benzylidene-β-benzyl-γ-butyrolactones using NaBH4–NiCl2. The reduction is found to proceed via conjugate addition of a hydride to an α-benzylidene-β-benzyl-γ-butyrolactone and the stereoselective protonation of the resulting metal enolate. The stereoselectivity would be brought about by the conformational rigidity of the phenyl moiety of the α-benzyl group induced by 1,3-allylic strain.

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