title: Asymmetric total synthesis of a pentacyclic Lycopodium alkaloid: huperzine-Q.
abstract: Right on Q: the first asymmetric total synthesis of (-)-huperzine-Q, which possesses six stereogenic centers and a spiroaminal moiety, has been achieved in 19 steps and 16.4 % overall yield. This synthesis involved a novel stereoselective Pauson-Khand reaction, a vinyl Claisen rearrangement, and a biomimetic spiroaminal formation. TBDPS=tert-butyldiphenylsilyl.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, Yayoi-cho, Inage-ku, Chiba, Japan.
authors.forename: Atsushi
authors.initials: A
authors.lastname: Nakayama
authors.forename: Noriyuki
authors.initials: N
authors.lastname: Kogure
authors.forename: Mariko
authors.initials: M
authors.lastname: Kitajima
authors.forename: Hiromitsu
authors.initials: H
authors.lastname: Takayama
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D032502:Lycopodium / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; D013141:Spiro Compounds; C578574:huperzine-Q