Synthesis of the Furanosteroidal Antibiotic Viridin

Authors

  • Edward A. Anderson Dr.,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, and the Department of Chemistry, Princeton University, Princeton, NJ 08544, USA, Fax: (+1) 609-258-1980
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    • These authors contributed equally to this work.

  • Erik J. Alexanian,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, and the Department of Chemistry, Princeton University, Princeton, NJ 08544, USA, Fax: (+1) 609-258-1980
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    • These authors contributed equally to this work.

  • Erik J. Sorensen Prof. Dr.

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, and the Department of Chemistry, Princeton University, Princeton, NJ 08544, USA, Fax: (+1) 609-258-1980
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  • This work was supported by the NIH (NIGMS GM065483), The Skaggs Foundation at TSRI, The Lindemann Trust, U.K. (E.A.A.), a Skaggs postdoctoral fellowship (E.A.A), a Skaggs predoctoral fellowship (E.J.A.), AstraZeneca, Eli Lilly, Pfizer, Merck Research Laboratories, and a Camille Dreyfus Teacher-Scholar Award (E.J.S.). We thank Dr. D.-H. Huang and Dr. L. Pasternack for assistance with NMR spectroscopy and Dr. G. Siuzdak for mass spectrometric analysis.

Abstract

original image

A rhodium-catalyzed alkyne cyclotrimerization, domino electrocyclic reactions, and a hydroxy-directed dihydroxylation are key steps in an efficient synthesis of the bioactive furanosteroid viridin (1) from a simple acyclic triyne.

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