Journal
CHINESE JOURNAL OF ORGANIC CHEMISTRY
Volume 41, Issue 7, Pages 2885-2890Publisher
SCIENCE PRESS
DOI: 10.6023/cjoc202102034
Keywords
Camptothecin; Pictet-Spengler reaction; oxa-Diels-Alder reaction; Winterfeldt oxidation; formal synthesis
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Funding
- National Natural Science Foundation of China [21871190]
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A concise biogenetically inspired formal synthesis of camptothecin has been developed, utilizing key reactions such as Pictet-Spengler reaction, intramolecular oxa-Diels-Alder reaction, and Winterfeldt biomimetic oxidation without the use of protecting groups.
A concise biogenetically inspired formal synthesis of camptothecin without use of protecting groups has been developed starting from tryptamine and easily prepared ethyl glutaconaldehyde salt. The synthesis features the key Pictet-Spengler reaction, efficient intramolecular oxa-Diels-Alder reaction to construct heptacyclic monoterpenoid indole alkaloid intermediate, as well as the following Winterfeldt biomimetic oxidation to form quinolinone moiety from indole skeleton.
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