Total Synthesis and Stereochemical Assignment of Baringolin†
Xavier Just-Baringo
Institute for Research in Biomedicine, Barcelona Science Park–University of Barcelona, Baldiri Reixac 10, 08028 Barcelona (Spain) http://www.pcb.ub.edu/fama/htm/home.htm
CIBER-BBN, Networking Centre on Bioengineering Biomaterials and Nanomedicine, 08028 Barcelona (Spain)
Search for more papers by this authorDr. Paolo Bruno
Institute for Research in Biomedicine, Barcelona Science Park–University of Barcelona, Baldiri Reixac 10, 08028 Barcelona (Spain) http://www.pcb.ub.edu/fama/htm/home.htm
CIBER-BBN, Networking Centre on Bioengineering Biomaterials and Nanomedicine, 08028 Barcelona (Spain)
Search for more papers by this authorDr. Lars K. Ottesen
Institute for Research in Biomedicine, Barcelona Science Park–University of Barcelona, Baldiri Reixac 10, 08028 Barcelona (Spain) http://www.pcb.ub.edu/fama/htm/home.htm
CIBER-BBN, Networking Centre on Bioengineering Biomaterials and Nanomedicine, 08028 Barcelona (Spain)
Search for more papers by this authorDr. Librada M. Cañedo
Instituto Biomar, S.A. Parque Tecnológico de Leon-M10.4, 24009 Armunia, León (Spain)
Search for more papers by this authorCorresponding Author
Prof. Fernando Albericio
Institute for Research in Biomedicine, Barcelona Science Park–University of Barcelona, Baldiri Reixac 10, 08028 Barcelona (Spain) http://www.pcb.ub.edu/fama/htm/home.htm
CIBER-BBN, Networking Centre on Bioengineering Biomaterials and Nanomedicine, 08028 Barcelona (Spain)
Department of Organic Chemistry, University of Barcelona, 08028 Barcelona (Spain)
Institute for Research in Biomedicine, Barcelona Science Park–University of Barcelona, Baldiri Reixac 10, 08028 Barcelona (Spain) http://www.pcb.ub.edu/fama/htm/home.htmSearch for more papers by this authorCorresponding Author
Prof. Mercedes Álvarez
Institute for Research in Biomedicine, Barcelona Science Park–University of Barcelona, Baldiri Reixac 10, 08028 Barcelona (Spain) http://www.pcb.ub.edu/fama/htm/home.htm
CIBER-BBN, Networking Centre on Bioengineering Biomaterials and Nanomedicine, 08028 Barcelona (Spain)
Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028 Barcelona (Spain)
Institute for Research in Biomedicine, Barcelona Science Park–University of Barcelona, Baldiri Reixac 10, 08028 Barcelona (Spain) http://www.pcb.ub.edu/fama/htm/home.htmSearch for more papers by this authorXavier Just-Baringo
Institute for Research in Biomedicine, Barcelona Science Park–University of Barcelona, Baldiri Reixac 10, 08028 Barcelona (Spain) http://www.pcb.ub.edu/fama/htm/home.htm
CIBER-BBN, Networking Centre on Bioengineering Biomaterials and Nanomedicine, 08028 Barcelona (Spain)
Search for more papers by this authorDr. Paolo Bruno
Institute for Research in Biomedicine, Barcelona Science Park–University of Barcelona, Baldiri Reixac 10, 08028 Barcelona (Spain) http://www.pcb.ub.edu/fama/htm/home.htm
CIBER-BBN, Networking Centre on Bioengineering Biomaterials and Nanomedicine, 08028 Barcelona (Spain)
Search for more papers by this authorDr. Lars K. Ottesen
Institute for Research in Biomedicine, Barcelona Science Park–University of Barcelona, Baldiri Reixac 10, 08028 Barcelona (Spain) http://www.pcb.ub.edu/fama/htm/home.htm
CIBER-BBN, Networking Centre on Bioengineering Biomaterials and Nanomedicine, 08028 Barcelona (Spain)
Search for more papers by this authorDr. Librada M. Cañedo
Instituto Biomar, S.A. Parque Tecnológico de Leon-M10.4, 24009 Armunia, León (Spain)
Search for more papers by this authorCorresponding Author
Prof. Fernando Albericio
Institute for Research in Biomedicine, Barcelona Science Park–University of Barcelona, Baldiri Reixac 10, 08028 Barcelona (Spain) http://www.pcb.ub.edu/fama/htm/home.htm
CIBER-BBN, Networking Centre on Bioengineering Biomaterials and Nanomedicine, 08028 Barcelona (Spain)
Department of Organic Chemistry, University of Barcelona, 08028 Barcelona (Spain)
Institute for Research in Biomedicine, Barcelona Science Park–University of Barcelona, Baldiri Reixac 10, 08028 Barcelona (Spain) http://www.pcb.ub.edu/fama/htm/home.htmSearch for more papers by this authorCorresponding Author
Prof. Mercedes Álvarez
Institute for Research in Biomedicine, Barcelona Science Park–University of Barcelona, Baldiri Reixac 10, 08028 Barcelona (Spain) http://www.pcb.ub.edu/fama/htm/home.htm
CIBER-BBN, Networking Centre on Bioengineering Biomaterials and Nanomedicine, 08028 Barcelona (Spain)
Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028 Barcelona (Spain)
Institute for Research in Biomedicine, Barcelona Science Park–University of Barcelona, Baldiri Reixac 10, 08028 Barcelona (Spain) http://www.pcb.ub.edu/fama/htm/home.htmSearch for more papers by this authorWe gratefully acknowledge support from the Spanish Science and Innovation Ministry, CICYT (CTQ2012-30930) and the Generalitat de Catalunya (2009SGR 1024). X.J. thanks ISCIII for a PFIS grant. We also thank Dr. Antonio Fernandez from Biomar SA for supplying a sample of the natural product for comparison.
Graphical Abstract
The thiopeptide antibiotic baringolin has been synthesized, and its structure and stereochemistry have been confirmed. The use of a strategy based on palladium-catalyzed cross-couplings permitted a modular construction of this natural product.
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