This research was supported by ETH and the Swiss National Science Foundation. A scholarship was provided by the Fonds der Chemischen Industrie (to F.K.). We are grateful for generous support of our program from Roche, Eli Lilly, and Boehringer Ingelheim. We thank Dr. Lee D. Fader for initial studies and Gabriela J. Marti for assistance with the synthesis of the C21–C25 fragment.
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Communication
Total Synthesis of Bafilomycin A1†
Article first published online: 9 DEC 2008
DOI: 10.1002/anie.200804645
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Kleinbeck, F. and Carreira, Erick M. (2009), Total Synthesis of Bafilomycin A1. Angew. Chem. Int. Ed., 48: 578–581. doi: 10.1002/anie.200804645
- †
Publication History
- Issue published online: 29 DEC 2008
- Article first published online: 9 DEC 2008
- Manuscript Received: 22 SEP 2008
Funded by
- ETH
- Swiss National Science Foundation
- Fonds der Chemischen Industrie
- Roche
- Eli Lilly
- Boehringer Ingelheim
Keywords:
- acetylides;
- asymmetric synthesis;
- natural products;
- nitrile oxides;
- total synthesis
A convergent synthesis of bafilomycin A1 (see structure) is presented, and relies on the Zn(OTf)2-mediated diastereoselective addition of alkynes to aldehydes. The coupling of a complex enyne with a sensitive aldehyde in the key step, in combination with a novel strategy for a chemoselective trans-reduction of the enyne, establishes an alternative to standard palladium-catalyzed cross-coupling strategies for the formation of 1,3-dienes.