title: The total synthesis of (+)-hapalindole Q by an organomediated Diels-Alder reaction.
abstract: The total synthesis of (+)-hapalindole Q has been achieved. The key step is a Diels-Alder reaction mediated by MacMillan's organocatalyst to provide the critical intermediate with high enantioselectivity (93% ee). This step establishes the proper arrangement of the required four contiguous stereocenters, including the quaternary center, and represents the first successful application of an enantioselective organomediated Diels-Alder reaction in total synthesis.
authors: Department of Chemistry, University of Western Ontario, London, Ontario, N6A 5B7, Canada.
authors: Aaron C
authors: AC
authors: Kinsman
authors: Michael A
authors: MA
authors: Kerr
mesh_terms: D000458:Cyanobacteria / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D007211:Indoles; C438931:hapalindole Q