Journal of Organic Chemistry p. 12664 - 12671 (2019)
Update date:2022-08-11
Topics:
Zhang, Qing
Zhang, Fu-Min
Zhang, Chang-Sheng
Liu, Si-Zhan
Tian, Jin-Miao
Wang, Shao-Hua
Zhang, Xiao-Ming
Tu, Yong-Qiang
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.
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