title: Formal synthesis of (±)-cycloclavine.
abstract: An efficient formal synthesis of (±)-cycloclavine is achieved in seven steps and 27% overall yield from the known 2-(4-bromo-1-tosyl-1H-indol-3-yl)acetaldehyde. Key features include an iron(III)-catalyzed aza-Cope-Mannich cyclization and an intramolecular Heck reaction or a self-terminating 6-exo-trig aryl radical-alkene cyclization.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou, 730000, P. R. China.
authors.forename: Wei
authors.initials: W
authors.lastname: Wang
authors.forename: Jia-Tian
authors.initials: JT
authors.lastname: Lu
authors.forename: Hao-Li
authors.initials: HL
authors.lastname: Zhang
authors.forename: Zi-Fa
authors.initials: ZF
authors.lastname: Shi
authors.forename: Jing
authors.initials: J
authors.lastname: Wen
authors.forename: Xiao-Ping
authors.initials: XP
authors.lastname: Cao
mesh_terms: D000079:Acetaldehyde / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D007501:Iron / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C000590895:2-(4-bromo-1-tosyl-1H-indol-3-yl)acetaldehy; D026121:Indole Alkaloids; D007211:Indoles; C560517:cycloclavine; D007501:Iron; D000079:Acetaldehyde