title: Asymmetric Total Synthesis of (-)-Lycospidine A.
abstract: The first asymmetric total synthesis of the structurally unique Lycopodium alkaloid (-)-lycospidine A, containing an unprecedented five-membered ring, has been accomplished in only 10 steps with 21.6% overall yield from the known conveniently available sulfoxide. This protecting-group-free short synthesis relied on the use of a key amidation/aza-Prins domino cyclization reaction to rapidly construct the tricyclic skeleton and two continuous stereocenters (one of which is a bridged quaternary stereocenter). An intramolecular aldol condensation was successfully utilized to establish the unique five-membered ring, and a late-stage oxidation inspired by biosynthesis pathway was adopted to synthesize the diosphenol ring of (-)-lycospidine A.
authors: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou 730000, People's Republic of China.
authors: Shiyan
authors: S
authors: Xu
authors: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou 730000, People's Republic of China.
authors: Jing
authors: J
authors: Zhang
authors: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou 730000, People's Republic of China.
authors: Donghui
authors: D
authors: Ma
authors: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou 730000, People's Republic of China.
authors: Dengyu
authors: D
authors: Xu
authors: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou 730000, People's Republic of China.
authors: Xingang
authors: X
authors: Xie
authors: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou 730000, People's Republic of China.|Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300071, People's Republic of China.
authors: Xuegong
authors: X
authors: She