期刊
BIOORGANIC & MEDICINAL CHEMISTRY
卷 27, 期 13, 页码 2991-2997出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2019.04.033
关键词
Natural product; Asymmetric synthesis; Enantioselectivity; Diels-Alder reaction
资金
- Fonds der Chemischen Industrie
- Deutsche Forschungsgemeinschaft [GRK2158]
- Ministry of Innovation, Science and Research of the German federal state of North-Rhine Westphalia
- Forschungszentrum Julich GmbH
- Heinrich-Heine-Universitat Dusseldorf
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.
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