This work was partially supported by Global COE program (Chemistry) and a Grant-in-Aid for Scientific Research (JSPS). We are grateful to Daiso Co. Ltd., Osaka, for the generous supply of (R)-(−)-epichlorohydrin.
First Stereoselective Total Synthesis of FD-594 Aglycon†
Article first published online: 3 APR 2009
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 48, Issue 19, pages 3462–3465, April 27, 2009
How to Cite
Masuo, R., Ohmori, K., Hintermann, L., Yoshida, S. and Suzuki, K. (2009), First Stereoselective Total Synthesis of FD-594 Aglycon. Angew. Chem. Int. Ed., 48: 3462–3465. doi: 10.1002/anie.200806338
- Issue published online: 23 APR 2009
- Article first published online: 3 APR 2009
- Manuscript Received: 27 DEC 2008
- Global COE program
- natural product synthesis;
- total synthesis
Stereocontrolled access to the hexacyclic core of FD-594 has been achieved. The key steps include the intramolecular SNAr reaction for construction of the densely functionalized xanthone skeleton, the stereoselective lactone cleavage using a chiral nucleophile to induce the axial stereochemistry, and the SmI2-mediated pinacol cyclization for the stereocontrolled conversion of axially chiral biaryl dialdehyde into the corresponding trans diol.