期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 52, 页码 18733-18736出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201604697
关键词
angucycline antibiotics; antitumor antibiotics; aquayamycin; natural products; total synthesis
资金
- MEXT
- JSPS KAKENHI [JP16H01161]
- Grants-in-Aid for Scientific Research [26282212, 16H01161] Funding Source: KAKEN
An efficient and practical total synthesis of aquayamycin has been accomplished. The highly oxidized and stereochemically complex tetracyclic ring system was constructed using three key reactions: 1) highly diastereo-selective 1,2-addition of C-glycosyl naphthyllithium to a cyclic ketone, 2) indium-mediated site-selective allylation-rearrangement sequence of naphthoquinone, and 3) diastereoselective intramolecular pinacol coupling. This synthetic strategy offers a novel and efficient pathway to prepare aquayamycin-type angucycline antibiotics.
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