title: Synthesis of the 10-azatricyclo[3.3.2.0(4,8)]decane core of C20-diterpenoid alkaloid racemulsonine via iodine(III) promoted transannular aziridination reaction.
abstract: The functionalized A/E/F ring system of C20-diterpenoid alkaloid racemulsonine has been efficiently synthesized. The Key steps involved a diastereoselective Au(I)-catalyzed annulation to form cis-fused cyclopentene and a PIDA promoted transannular aziridination of primary amine followed by regio- and stereoselective ring cleavage of bridged aziridine.
authors.affiliation: Key Laboratory of Drug Targeting, Ministry of Education, and Department of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University, No. 17, Duan 3, Renmin Nan Road, Chengdu 610041, PR China.
authors.forename: Ru-Huai
authors.initials: RH
authors.lastname: Mei
authors.forename: Zhi-Gang
authors.initials: ZG
authors.lastname: Liu
authors.forename: Hang
authors.initials: H
authors.lastname: Cheng
authors.forename: Liang
authors.initials: L
authors.lastname: Xu
authors.forename: Feng-Peng
authors.initials: FP
authors.lastname: Wang
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C583650:10-azatricyclo(3.3.2.0(4,8))decane; D000470:Alkaloids; D001388:Aziridines; D004224:Diterpenes; D006575:Heterocyclic Compounds, 3-Ring; C033132:aziridine