title: Synthesis of the carbon framework of scholarisine A by intramolecular oxidative coupling.
abstract: Scholarisine A, isolated from the leaves of Alstonia scholaris, is a monoterpene indole alkaloid with an unprecedented cage-like structure. In this paper, preparation of the distinctive cage-like core skeleton of scholarisine A is described. The key feature of this synthetic strategy is an intramolecular oxidative coupling reaction at the late stage to construct a 10-oxa-tricyclo[5.3.1.0(3, 8)]undecan-9-one structure fused with indolenine. Intramolecular oxidative coupling by using N-iodosuccinimide gave the carbon framework of scholarisine A in moderate yield, which is the first example of intramolecular oxidative-coupling reaction between non-activated enolate and indole. This study lays the foundation for continued investigations towards the total synthesis of scholarisine A.
authors: Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1, Tanabe-dori, Mizuho-ku, Nagoya, 467-8603, Japan.
authors: Tsugunori
authors: T
authors: Watanabe
authors: Nobuki
authors: N
authors: Kato
authors: Naoki
authors: N
authors: Umezawa
authors: Tsunehiko
authors: T
authors: Higuchi
mesh_terms: D031051:Alstonia / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D015394:Molecular Structure; D039821:Monoterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D058451:Oxidative Coupling; D018515:Plant Leaves / Q000737:chemistry
chemical_list: D026121:Indole Alkaloids; D039821:Monoterpenes; C528219:scholarisine A