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We thank the EPSRC and GSK for support of this project. We thank Ben Whitehurst for technical assistance.
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Communication
Stereoselective Total Synthesis of (+)-Giganin and Its C10 Epimer by Using Late-Stage Lithiation–Borylation Methodology†
Article first published online: 25 JAN 2013
DOI: 10.1002/anie.201208403
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
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
- †
Publication History
- Issue published online: 19 FEB 2013
- Article first published online: 25 JAN 2013
- Manuscript Received: 18 OCT 2012
Funded by
- EPSRC
- GSK
Keywords:
- borylation;
- carbamate;
- giganin;
- lithiation;
- 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.