Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 32, Pages 10127-10131Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201804329
Keywords
iron; natural product synthesis; radical cyclization; spiro compounds
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Funding
- National Natural Science Foundation of China [81274066]
- CAMS Innovation Fund for Medical Sciences (CIFMS) [2016-I2M-1-010]
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The first synthesis of polyflavanostilbeneB (1), which has seven contiguous stereocenters including two quaternary carbon centers, from abundant polymeric (-)-epicatechin gallate on a gram scale in three steps without the use of protecting groups is reported. The key transformations of this strategy include a regioselective and stereoselective substitution of resveratrol to give the 4-derivative of (-)-epicatechin 3-gallate and an iron-catalyzed cyclization reaction. The possible radical cyclization mechanism in the formation of the hexahydrocyclopenta[c]furan core is also discussed.
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