TY  - JOUR
AU  - Mechsner, Bastian
AU  - Böse, Dietrich
AU  - Hogenkamp, Fabian
AU  - Ledermann, Nadia
AU  - Hartmann, Rudolf
AU  - Bochinsky, Kevin
AU  - Frey, Wolfgang
AU  - Pietruszka, Jörg
TI  - Enantioselective total synthesis of altersolanol A and N
JO  - Bioorganic & medicinal chemistry
VL  - 27
IS  - 13
SN  - 0968-0896
CY  - Amsterdam [u.a.]
PB  - Elsevier
M1  - FZJ-2019-04246
SP  - 2991 - 2997
PY  - 2019
AB  - 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.
LB  - PUB:(DE-HGF)16
C6  - pmid:31072649
UR  - <Go to ISI:>//WOS:000470106900027
DO  - DOI:10.1016/j.bmc.2019.04.033
UR  - https://juser.fz-juelich.de/record/864465
ER  -