title: Total synthesis of chaetoquadrins A-C.
abstract: The first total synthesis of the monoamine oxidase inhibitors chaetoquadrins A-C has been accomplished. Key steps in the synthesis include an aromatic Claisen rearrangement, asymmetric boron aldol reaction and acid-mediated spiroketalization. Comparison of spectral data for the synthetic spiroketals confirmed the proposed structure for these natural products.
authors: School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland, New Zealand.
authors: U Bin
authors: UB
authors: Kim
authors: Daniel P
authors: DP
authors: Furkert
authors: Margaret A
authors: MA
authors: Brimble
mesh_terms: D001203:Ascomycota / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D008996:Monoamine Oxidase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D001688:Biological Products; D006576:Heterocyclic Compounds, 4 or More Rings; D007783:Lactones; D008996:Monoamine Oxidase Inhibitors; D013141:Spiro Compounds; C581424:chaetoquadrin A; C581425:chaetoquadrin B; C581426:chaetoquadrin C