title: Copper-catalyzed radical cyclization to access 3-hydroxypyrroloindoline: biomimetic synthesis of protubonine A.
abstract: An unprecedented copper-catalyzed intramolecular radical cyclization was developed for the synthesis of 3-hydroxypyrroloindoline skeletons in excellent yields. The 3-hydroxyl group was introduced by trapping the radical intermediate with molecular oxygen or TEMPO. This process represents a unique radical oxidation pathway for tryptamine/tryptophan derivatives and allows a rapid biomimetic synthesis of natural product protubonine A.
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, Yunnan, China.
authors.forename: Xu
authors.initials: X
authors.lastname: Deng
authors.forename: Kangjiang
authors.initials: K
authors.lastname: Liang
authors.forename: Xiaogang
authors.initials: X
authors.lastname: Tong
authors.forename: Ming
authors.initials: M
authors.lastname: Ding
authors.forename: Dashan
authors.initials: D
authors.lastname: Li
authors.forename: Chengfeng
authors.initials: C
authors.lastname: Xia
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D032701:Biomimetics; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D054659:Diketopiperazines / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014364:Tryptophan
chemical_list: D000470:Alkaloids; D054659:Diketopiperazines; D007211:Indoles; C560175:protubonine A; D003300:Copper; D014364:Tryptophan