title: Synthetic study toward the misassigned (±)-tronoharine.
abstract: The synthesis of a pentacyclic indole compound corresponding to the core structure of the misassigned indole alkaloid, tronoharine (1), is presented. The key reactions were a formal [3 + 3] cycloaddition of an indol-2-yl carbinol with an azadiene for the construction of the 6/5/6/6 tetracyclic system containing an all-carbon quaternary center and an intramolecular substitution reaction of an amine and a triflate for the creation of the bridged azepine ring. In addition, some other interesting transformations discovered during the synthetic studies are also discussed.
authors.affiliation: Key Lab of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences , 5625 Renmin Street, Changchun 130022, China.
authors.forename: Xue
authors.initials: X
authors.lastname: Zhong
authors.forename: You
authors.initials: Y
authors.lastname: Li
authors.forename: Jing
authors.initials: J
authors.lastname: Zhang
authors.forename: Fu-She
authors.initials: FS
authors.lastname: Han
mesh_terms: D001381:Azepines / Q000737:chemistry; D003500:Cyclization; D061565:Cycloaddition Reaction; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D008296:Malaysia; D013237:Stereoisomerism; D030014:Tabernaemontana / Q000737:chemistry
chemical_list: D001381:Azepines; D026121:Indole Alkaloids; C000596576:tronoharine