Journal
CHINESE JOURNAL OF CHEMISTRY
Volume 38, Issue 11, Pages 1339-1352Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.202000293
Keywords
Nortriterpenoid; Biomimetic synthesis; Remote C-H functionalization; Ring expansion; Cascade reaction
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Funding
- National Natural Science Foundation of China [21871289, 21672245]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- CAS Key Laboratory of Synthetic Chemistry of Natural Substances
- Shanghai Institute of Organic Chemistry
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The Summary of main observation and conclusion The natural product propindilactone G is a complexSchisandranortriterpenoid with a unique 5/5/7/6/5 pentacyclic framework. This full paper describes the development of concise biomimetic synthesis of propindilactone G from a known steroid lactone. The key C19-OH intermediate was synthesizedviaBreslow and Suarez radical remote C-H functionalizations. Wagner-Meerwein rearrangement was subsequently utilized for the expansion of the B ring. To invert the configuration of the C10 tertiary alcohol, an intramolecular peroxide cyclization catalyzed by BF3 center dot Et2O was devised. The 5/5 fused lactone system was then assembled in a biomimetic transesterification/oxa-Michael addition sequence. Our work should provide experimental support for the proposed biosynthetic pathway and facilitate investigation of the biological activities of propindilactone G.
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