title: Enantioselective Synthesis of 2,3-Disubstituted Benzomorpholines: Analogues of Lignan Natural Products.
abstract: The enantioselective synthesis of 2,3-disubstituted benzomorpholines, analogues of 1,4-benzodioxane natural products, has been achieved via addition of electron-rich aromatic donors to acyl-iminium ions derived from benzomorpholine aminols. Subsequent modification of the benzomorpholine scaffold allows side chains mimicking those found in 1,4-benzodioxane lignans to be added. Antiproliferative testing of the prepared analogues showed promising results against MDA-MB-231 and HCT116 cancer cell lines.
authors: School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland, New Zealand.
authors: Eun-Kyung
authors: EK
authors: Jung
authors: School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland, New Zealand.
authors: Lisa I
authors: LI
authors: Pilkington
authors: School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland, New Zealand.
authors: David
authors: D
authors: Barker
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D017705:Lignans / Q000737:chemistry*; D009025:Morpholines / Q000138:chemical synthesis* / Q000737:chemistry; D066244:Proton Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D017705:Lignans; D009025:Morpholines