%0 Journal Article
%A Mechsner, Bastian
%A Böse, Dietrich
%A Hogenkamp, Fabian
%A Ledermann, Nadia
%A Hartmann, Rudolf
%A Bochinsky, Kevin
%A Frey, Wolfgang
%A Pietruszka, Jörg
%T Enantioselective total synthesis of altersolanol A and N
%J Bioorganic & medicinal chemistry
%V 27
%N 13
%@ 0968-0896
%C Amsterdam [u.a.]
%I Elsevier
%M FZJ-2019-04246
%P 2991 - 2997
%D 2019
%X The development of the first enantioselective total synthesis of altersolanol N is reported. The decisive step of the synthesis is the enantioselective formation of the tetrahydroanthraquinone nucleus by a [4 + 2]-cycloaddition in high yield and with excellent diastereo- and enantioselectivity (>95:5 dr and 95:5 er). In addition, a demanding selective monoacetylation of the OH group at the C-2 position was achieved: an epoxide ring opening with the participation of a neighbouring acetyl group could be established. The route proved to be an efficient alternative to also access enantiomerically pure altersolanol A.
%F PUB:(DE-HGF)16
%9 Journal Article
%$ pmid:31072649
%U <Go to ISI:>//WOS:000470106900027
%R 10.1016/j.bmc.2019.04.033
%U https://juser.fz-juelich.de/record/864465