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Dr. Yusuke Kasai, Naoki Michihata, Hidehisa Nishimura, Tsukasa Hirokane and Prof. Dr. Hidetoshi Yamada Total Synthesis of (+)-Davidiin Angewandte Chemie International Edition 51

Version of Record online: 2 JUL 2012 | DOI: 10.1002/anie.201203305

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Quite strained: The total synthesis of (+)-davidiin, an ellagitannin with more substituents in axial than in equatorial positions, requires a conformational lock of the glucose, induced by steric repulsion between adjacent bulky silyloxy groups. This conformational lock played a pivotal role in 1) the β-selective formation of the glycosyl ester at the anomeric position, 2) the formation of the 1,6-HHDP bridge, and 3) the complete control of axial chirality in the aryl–aryl coupling.

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