Total synthesis of (-)-anominine.
The first total synthesis of anominine has been achieved, and the absolute configuration of the product has been determined. The key features include the development of a new, highly efficient organocatalyzed method for the asymmetric synthesis of Wieland-Miescher ketone building blocks, an unusual selenoxide [2,3]-sigmatropic rearrangement, and a ZrCl(4)-catalyzed indole coupling as well as several chemoselective transformations controlled by the structurally congested nature of the bicyclic core.
Bradshaw
Ben
B
Laboratori de Química Orgànica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII s/n, 08028 Barcelona, Spain. benbradshaw@ub.edu
Etxebarria-Jardí
Gorka
G
Bonjoch
Josep
J
D000475:Alkenes / Q000138:chemical synthesis*; D001230:Aspergillus / Q000378:metabolism*; D001685:Biological Factors / Q000138:chemical synthesis*; D004224:Diterpenes / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis*
D000475:Alkenes; D001685:Biological Factors; D004224:Diterpenes; D007211:Indoles; C550942:anominine