Total Synthesis and Structural Revision of Viridicatumtoxin B†
Corresponding Author
Prof. Dr. K. C. Nicolaou
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
Department of Chemistry and Biochemistry, University of California, San Diego 9500 Gilman Drive, La Jolla, CA 92093 (USA)
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)Search for more papers by this authorDr. Christian Nilewski
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
Department of Chemistry and Biochemistry, University of California, San Diego 9500 Gilman Drive, La Jolla, CA 92093 (USA)
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
These authors contributed equally to this work.
Search for more papers by this authorChristopher R. H. Hale
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
Department of Chemistry and Biochemistry, University of California, San Diego 9500 Gilman Drive, La Jolla, CA 92093 (USA)
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
These authors contributed equally to this work.
Search for more papers by this authorDr. Heraklidia A. Ioannidou
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
Department of Chemistry and Biochemistry, University of California, San Diego 9500 Gilman Drive, La Jolla, CA 92093 (USA)
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
Search for more papers by this authorDr. Abdelatif ElMarrouni
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
Department of Chemistry and Biochemistry, University of California, San Diego 9500 Gilman Drive, La Jolla, CA 92093 (USA)
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
Search for more papers by this authorLizanne G. Koch
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
Department of Chemistry and Biochemistry, University of California, San Diego 9500 Gilman Drive, La Jolla, CA 92093 (USA)
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. K. C. Nicolaou
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
Department of Chemistry and Biochemistry, University of California, San Diego 9500 Gilman Drive, La Jolla, CA 92093 (USA)
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)Search for more papers by this authorDr. Christian Nilewski
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
Department of Chemistry and Biochemistry, University of California, San Diego 9500 Gilman Drive, La Jolla, CA 92093 (USA)
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
These authors contributed equally to this work.
Search for more papers by this authorChristopher R. H. Hale
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
Department of Chemistry and Biochemistry, University of California, San Diego 9500 Gilman Drive, La Jolla, CA 92093 (USA)
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
These authors contributed equally to this work.
Search for more papers by this authorDr. Heraklidia A. Ioannidou
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
Department of Chemistry and Biochemistry, University of California, San Diego 9500 Gilman Drive, La Jolla, CA 92093 (USA)
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
Search for more papers by this authorDr. Abdelatif ElMarrouni
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
Department of Chemistry and Biochemistry, University of California, San Diego 9500 Gilman Drive, La Jolla, CA 92093 (USA)
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
Search for more papers by this authorLizanne G. Koch
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
Department of Chemistry and Biochemistry, University of California, San Diego 9500 Gilman Drive, La Jolla, CA 92093 (USA)
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
Search for more papers by this authorFinancial support was provided by the National Institutes of Health (USA) (grant AI055475-11) and the Skaggs Institute of Research. Fellowships to C.N. (Feodor Lynen Research Fellowship, Alexander von Humboldt Foundation), C.R.H.H. (NSF Graduate Research Fellowship), and A.E. (Fundación Alfonso Martín Escudero) are gratefully appreciated. We thank Dr. R. K. Chadha for X-ray crystallographic assistance and Dr. D. H. Huang and Dr. L. Pasternack for NMR spectroscopic assistance. We thank Prof. W.-G. Kim for graciously providing scanned NMR spectra of natural viridicatumtoxin B.
Graphical Abstract
Will the real viridicatumtoxin B please stand up: The total synthesis of viridicatumtoxin B resulted in its structural revision and opens the way for analogue construction and biological evaluation of this complex tetracycline-like antibiotic. The highly convergent strategy employed allows for swift construction of the entire carbocyclic framework of the molecule.
Supporting Information
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