We thank the EPSRC and GSK for support of this project. We thank Ben Whitehurst for technical assistance.
Stereoselective Total Synthesis of (+)-Giganin and Its C10 Epimer by Using Late-Stage Lithiation–Borylation Methodology†
Article first published online: 25 JAN 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 9, pages 2503–2506, February 25, 2013
How to Cite
Fletcher, C. J., Wheelhouse, K. M. P. and Aggarwal, V. K. (2013), Stereoselective Total Synthesis of (+)-Giganin and Its C10 Epimer by Using Late-Stage Lithiation–Borylation Methodology . Angew. Chem. Int. Ed., 52: 2503–2506. doi: 10.1002/anie.201208403
- Issue published online: 19 FEB 2013
- Article first published online: 25 JAN 2013
- Manuscript Received: 18 OCT 2012
- total synthesis
The first total synthesis of (+)-giganin and its unnatural diastereoisomer (+)-C10-epi-giganin has been completed in a total of 13 linear steps, and 7 % and 8 % overall yield, respectively (see scheme; (-)-sp= (-)-sparteine, (+)-sps=(+)-sparteine surrogate). Lithiation–borylation methodology has been successfully applied in the key step, to couple together advanced intermediates with very high diastereoselectivity, thus demonstrating its power as a tool for total synthesis.