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Catalytic Asymmetric Total Syntheses of (−)-Galanthamine and (−)-Lycoramine

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journal contribution
posted on 18.09.2019, 17:36 by Qing Zhang, Fu-Min Zhang, Chang-Sheng Zhang, Si-Zhan Liu, Jin-Miao Tian, Shao-Hua Wang, Xiao-Ming Zhang, Yong-Qiang Tu
The catalytic asymmetric total syntheses of the biologically important and therapeutically valuable Amaryllidaceae alkaloids (−)-galanthamine and (−)-lycoramine have been divergently achieved from commercially available 3-butyn-1-ol. A newly developed spirocyclic pyrrolidine (SPD)-catalyzed enantioselective Robinson annulation rapidly constructs the key cis-hydrodibenzofuran core, which bears an all-carbon quaternary stereocenter of the target molecules with an excellent stereoselective control. Additionally, the current asymmetric synthetic strategy provides an alternative approach toward the syntheses of (−)-galanthamine and its analogues.