We thank Prof. Tsutomu Hatano (Okayama University (Japan)) for identification of natural davidiin. We also thank Dr. Yasuko Okamoto (Tokushima Bunri University) for the recording of FAB mass spectra. Kakenhi and a SUNBOR grant partially supported this work.
Total Synthesis of (+)-Davidiin†
Article first published online: 2 JUL 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 32, pages 8026–8029, August 6, 2012
How to Cite
Kasai, Y., Michihata, N., Nishimura, H., Hirokane, T. and Yamada, H. (2012), Total Synthesis of (+)-Davidiin. Angew. Chem. Int. Ed., 51: 8026–8029. doi: 10.1002/anie.201203305
- Issue published online: 1 AUG 2012
- Article first published online: 2 JUL 2012
- Manuscript Received: 30 APR 2012
- medium-sized rings;
- natural products;
- total synthesis
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.