title: The asymmetric total synthesis of (+)-N-acetyl norloline.
abstract: The asymmetric total synthesis of (+)-N-acetyl norloline, the putative biogenic precursor of all known loline alkaloids, has been achieved in 12 steps from commercially available (R)-glyceraldehyde acetonide. The synthesis relies on the Rassu/Casiraghi's vinylogous aldol reaction, an intramolecular oxa-heteroconjugate addition and a reductive amination to establish the four contiguous stereogenic centers and construct the strained oxygen-bridge under mild conditions.
authors.affiliation: Department of Chemistry, Fujian Provincial Key Laboratory of Chemical Biology, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. China. pqhuang@xmu.edu.cn yejl@xmu.edu.cn.
authors.forename: Jian-Liang
authors.initials: JL
authors.lastname: Ye
authors.forename: Yang
authors.initials: Y
authors.lastname: Liu
authors.forename: Zhi-Ping
authors.initials: ZP
authors.lastname: Yang
authors.forename: Pei-Qiang
authors.initials: PQ
authors.lastname: Huang
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D005985:Glyceraldehyde / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000470:Alkaloids; D001952:Bridged-Ring Compounds; C000611700:N-acetyl norloline; C459241:glyceraldehyde acetonide; D005985:Glyceraldehyde