title: Total syntheses of lycoposerramine-V and 5-epi-lycoposerramine-V.
abstract: Enantioselective total syntheses of lycopodium alkaloids lycoposerramine-V and 5-epi-lycoposerramine-V have been accomplished. Features of the newly established total synthesis include: 1) introduction of the first chiral center with a scalable desymmetrization reaction of an meso-anhydride; 2) chemoselective functionalization of a bis-Weinreb-amide with Grignard addition; and 3) construction of the multifunctionalized cyclohexanone with a stereoselective intramolecular Michael addition.
authors.affiliation: State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing National Laboratory of Microstructures, Nanjing University, 22 Hankou Road, Nanjing 210093 (P. R. China).
authors.forename: Lan-De
authors.initials: LD
authors.lastname: Zhang
authors.forename: Ting-Ting
authors.initials: TT
authors.lastname: Zhou
authors.forename: Sen-Xing
authors.initials: SX
authors.lastname: Qi
authors.forename: Jie
authors.initials: J
authors.lastname: Xi
authors.forename: Xiao-Liang
authors.initials: XL
authors.lastname: Yang
authors.forename: Zhu-Jun
authors.initials: ZJ
authors.lastname: Yao
mesh_terms: D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D066244:Proton Magnetic Resonance Spectroscopy; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
chemical_list: D010880:Piperidines; D011804:Quinolines; C523753:lycoposerramine-V
keywords: Michael addition; alkaloids; chemoselectivity; lycoposerramine-V; total synthesis