title: Protecting-Group-Free Total Synthesis of (-)-Lycopodine via Phosphoric Acid Promoted Alkyne Aza-Prins Cyclization.
abstract: A protecting-group-free route for the total synthesis of (-)-lycopodine was demonstrated in only 8 steps from Wade's fawcettimine enone (12 steps from commercial availiable (R)-(+)-pulegone). The key core of this alkaloid was constructed through a phosphoric acid promoted and highly stereocontrolled alkyne aza-Prins cyclization reaction, synchronously establishing the bridged B-ring and the C13 quaternary stereocenter. Importantly, the synthesis further features a new efficient approach for the preparation of other lycopodine-type alkaloids.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , 222 TianShui South Road, Lanzhou 730000, China.
authors.forename: Donghui
authors.initials: D
authors.lastname: Ma
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , 222 TianShui South Road, Lanzhou 730000, China.
authors.forename: Zhuliang
authors.initials: Z
authors.lastname: Zhong
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , 222 TianShui South Road, Lanzhou 730000, China.
authors.forename: Zaimin
authors.initials: Z
authors.lastname: Liu
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , 222 TianShui South Road, Lanzhou 730000, China.
authors.forename: Mingjie
authors.initials: M
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , 222 TianShui South Road, Lanzhou 730000, China.
authors.forename: Shiyan
authors.initials: S
authors.lastname: Xu
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , 222 TianShui South Road, Lanzhou 730000, China.
authors.forename: Dengyu
authors.initials: D
authors.lastname: Xu
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , 222 TianShui South Road, Lanzhou 730000, China.
authors.forename: Dengpeng
authors.initials: D
authors.lastname: Song
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , 222 TianShui South Road, Lanzhou 730000, China.
authors.forename: Xingang
authors.initials: X
authors.lastname: Xie
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , 222 TianShui South Road, Lanzhou 730000, China.|Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China.
authors.forename: Xuegong
authors.initials: X
authors.lastname: She