title: Synthesis of γ-monofluorinated goniothalamin analogues via regio- and stereoselective ring-opening hydrofluorination of epoxide.
abstract: A stereoselective synthesis of the biologically interesting γ-monofluorinated goniothalamin analogue 2a was described. The features of the synthesis included regioselective reduction of the unprotected hydroxypropynyl moiety of compound 10 by Red-Al, asymmetric Sharpless epoxidation of allyl alcohol 11, and regio- and stereoselective ring-opening hydrofluorination of the hydroxypropynyl epoxide 14 with Et(3)N·3HF in high ee and dr. The chiral hydroxypropynyl fluorohydrin 15 was used as a valuable building block for preparation of a range of γ-monofluorinated α,β-unsaturated δ-lactones.
authors: College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai 201620, China.
authors: Jun-Ling
authors: JL
authors: Chen
authors: Feng
authors: F
authors: Zheng
authors: Yangen
authors: Y
authors: Huang
authors: Feng-Ling
authors: FL
authors: Qing
mesh_terms: D004852:Epoxy Compounds / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D006845:Hydrocarbons, Fluorinated; D007783:Lactones; D011753:Pyrones; C103280:goniothalamin