This title appears in the Scientific Report :
2019
Please use the identifier:
http://dx.doi.org/10.1016/j.bmc.2019.04.033 in citations.
Enantioselective total synthesis of altersolanol A and N
Enantioselective total synthesis of altersolanol A and N
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 (>...
Saved in:
Personal Name(s): | Mechsner, Bastian |
---|---|
Böse, Dietrich / Hogenkamp, Fabian / Ledermann, Nadia / Hartmann, Rudolf / Bochinsky, Kevin / Frey, Wolfgang / Pietruszka, Jörg (Corresponding author) | |
Contributing Institute: |
Strukturbiochemie; ICS-6 Biotechnologie; IBG-1 Institut für Bioorganische Chemie (HHUD); IBOC |
Published in: | Bioorganic & medicinal chemistry, 27 (2019) 13, S. 2991 - 2997 |
Imprint: |
Amsterdam [u.a.]
Elsevier
2019
|
PubMed ID: |
31072649 |
DOI: |
10.1016/j.bmc.2019.04.033 |
Document Type: |
Journal Article |
Research Program: |
Biotechnology |
Publikationsportal JuSER |
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. |