Stereoselective Syntheses of Cis- and Trans-Isomers of α-Hydroxy-α,β-dibenzyl-γ-butyrolactone Lignans: New Syntheses of (±)-Trachelogenin and (±)-Guayadequiol
journal contributionposted on 04.10.1996 by Yasunori Moritani, Chiaki Fukushima, Tatsuzo Ukita, Toshikazu Miyagishima, Hiroshi Ohmizu, Tameo Iwasaki
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Cis- and trans-isomers of α-hydroxy-α,β-dibenzyl-γ-butyrolactone lignans 1a,d−g and 2a,c,d were stereoselectively synthesized in good yields based on the electrophilic addition to the metal enolate of α-benzyl-γ-butyrolactone derivatives 1l−o and 3 as a key step. This method was applied to the syntheses of (±)-trachelogenin and (±)-guayadequiol, representative examples of the trans- and cis-isomers of α-hydroxy-α,β-dibenzyl-γ-butyrolactone lignan series.