title: Total Synthesis of Gelsedilam by Means of a Thiol-Mediated Diastereoselective Conjugate Addition-Aldol Reaction.
abstract: The total synthesis of gelsedilam, which features a highly diastereoselective thiol conjugate addition-intramolecular aldol reaction to install the strained and caged [3.2.2] bridged ring system and highly efficient NiCl2/NaBH4-mediated four-step transformation in one-pot to construct its five-membered lactam ring is reported. The synthesis requires only 18 linear steps from the known compounds, providing useful strategies for the construction of the intricate ring system in the synthesis of related gelsedine-type alkaloids.
authors.affiliation: Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
authors.forename: You-Ming
authors.initials: YM
authors.lastname: Huang
authors.affiliation: Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
authors.forename: Yang
authors.initials: Y
authors.lastname: Liu
authors.affiliation: Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
authors.forename: Chang-Wu
authors.initials: CW
authors.lastname: Zheng
authors.affiliation: Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
authors.forename: Qiao-Wen
authors.initials: QW
authors.lastname: Jin
authors.affiliation: Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
authors.forename: Lu
authors.initials: L
authors.lastname: Pan
authors.affiliation: Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
authors.forename: Ren-Ming
authors.initials: RM
authors.lastname: Pan
authors.affiliation: Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
authors.forename: Jun
authors.initials: J
authors.lastname: Liu
authors.affiliation: Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
authors.forename: Gang
authors.initials: G
authors.lastname: Zhao
keywords: aldol reaction; alkaloids; gelsedilam; gelsedine; total synthesis