First enantioselective total synthesis of altersolanol A. Issue 41 (4th October 2018) - Mechsner, Bastian
Abstract : The first enantioselective total synthesis of altersolanol A was accomplished by Diels–Alder cycloaddition promoted by ( R )-3, 3′-BINOL/boron Lewis acid. Abstract : The first enantioselective total synthesis of altersolanol A, a secondary metabolite from the endophytic fungi Stemphylium globuliferum and Alternaria solani, is described. The key step towards the tetrahydroanthraquinone core was an asymmetric Diels – Alder (D–A) cycloaddition promoted by ( R )-3, 3′-diphenyl-BINOL/boron Lewis acid with good to excellent yields and excellent diastereo- and enantioselectivity (>95 : 5 dr and 98 : 2 er).