title: Total synthesis of (-)-8-deoxyserratinine via an efficient Helquist annulation and double N-alkylation reaction.
abstract: The first enantioselective total synthesis of (-)-8-deoxyserratinine has been achieved in 15 steps from enone 4 with 7% overall yield. The key features include a highly efficient Helquist annulation to furnish the cis-fused 6/5 bicycle, facile construction of the aza nine-membered ring system employing double N-alkylation strategy, as well as asymmetric Shi epoxidation, delivering the desired beta-epoxide stereospecifically.
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650204, China. yangyurong@mail.kib.ac.cn
authors.forename: Yu-Rong
authors.initials: YR
authors.lastname: Yang
authors.forename: Zeng-Wei
authors.initials: ZW
authors.lastname: Lai
authors.forename: Liang
authors.initials: L
authors.lastname: Shen
authors.forename: Jiu-Zhong
authors.initials: JZ
authors.lastname: Huang
authors.forename: Xing-De
authors.initials: XD
authors.lastname: Wu
authors.forename: Jun-Lin
authors.initials: JL
authors.lastname: Yin
authors.forename: Kun
authors.initials: K
authors.lastname: Wei
mesh_terms: D000478:Alkylation; D004852:Epoxy Compounds / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D032502:Lycopodium / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C553068:8-deoxyserratinine; D004852:Epoxy Compounds; D007212:Indolizines