Tetrahedron p. 1793 - 1806 (1993)
Update date:2022-08-05
Topics: Retrosynthetic analysis Purification and characterization Scale-up and optimization Final steps Synthesis of Key Intermediates Biological Evaluation Asymmetric Hydrogenation Functional Group Protection Selection of Chiral Ligand and Catalyst Deprotection and Further Elaboration
Morimoto, Toshiaki
Chiba, Mitsuo
Achiwa, Kazuo
Optically pure (R)-arylmethylsuccinic acid mono-methyl esters were obtained efficiently by using the catalytic asymmetric hydrogenation of arylidenesuccinic acid monoesters with a rhodium(I) complex of a chiral bisphosphine, (4S,5S)-MOD-DIOP.Asymmetric total syntheses of some naturally occurring lignans, (+)-collinusin, (-)-deoxypodophyllotoxin, and (+)-neoisostegane, were achieved via several steps from (R)-γ-butyrolactones as key intermediates obtained by reduction of (R)-arylmethylsuccinic acid mono methyl-esters.
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