期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 12, 页码 3115-3119出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201311112
关键词
C-H activation; lignan; natural products; total synthesis
资金
- UC-Berkeley
- NSF [DGE-1106400]
A short total synthesis of podophyllotoxin, the prototypical aryltetralin lignan natural product, is reported. Key to the success of this synthetic pathway is a Pd-catalyzed C(sp(3))-H arylation reaction enabled by a conformational biasing element to promote C-C reductive elimination over an alternative CN bond-forming pathway. This strategy allows for access to the natural product in five steps from commercially available bromopiperonal, and sheds light on subtle conformational effects governing reductive elimination pathways from high-valent palladium centers.
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