We thank the National Basic Research Program of China (973 Program: 2010CB833200),the NSFC (21172100), the Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT: IRT1138), and “111” Program of MOE for financial support.
Total Synthesis of (−)-Jiadifenin†
Article first published online: 24 AUG 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 39, pages 9825–9828, September 24, 2012
How to Cite
Yang, Y., Fu, X., Chen, J. and Zhai, H. (2012), Total Synthesis of (−)-Jiadifenin . Angew. Chem. Int. Ed., 51: 9825–9828. doi: 10.1002/anie.201203176
- Issue published online: 19 SEP 2012
- Article first published online: 24 AUG 2012
- Manuscript Received: 25 APR 2012
- Pauson–Khand reaction;
- total synthesis
As easy as ABCD: (−)-Jiadifenin was synthesized in eighteen reaction steps from 1-[(E)-(4′-bromo-2′-butenyl)oxy]-4-methoxybenzene. Key features of this synthesis include: 1) Ireland–Claisen rearrangement to produce the two contiguous quaternary centers at C5 and C6 simultaneously, 2) intramolecular Pauson–Khand reaction (IMPKR) to concurrently construct the A and B rings, and 3) [2+2] photo-cycloaddition to generate the all-carbon quaternary center at C9.