Communication

Mechanism of the Vinylcyclobutane Rearrangement of Sceptrin to Ageliferin and Nagelamide E†

  1. Brian H. Northrop2,
  2. Daniel P. O'Malley1,
  3. Alexandros L. Zografos Dr.1,
  4. Phil S. Baran Prof.1,
  5. K. N. Houk Prof.2

Article first published online: 16 MAY 2006

DOI: 10.1002/anie.200600514

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 45, Issue 25, pages 4126–4130, June 19, 2006

Additional Information

How to Cite

Northrop, B. H., O'Malley, D. P., Zografos, A. L., Baran, P. S. and Houk, K. N. (2006), Mechanism of the Vinylcyclobutane Rearrangement of Sceptrin to Ageliferin and Nagelamide E. Angewandte Chemie International Edition, 45: 4126–4130. doi: 10.1002/anie.200600514

Author Information

  1. 1

    Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7375

  2. 2

    Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095, USA, Fax: (+1) 310-206-1843

  1. †

    We thank Dr. D. H. Huang and Dr. L. Pasternack for assistance with the NMR spectroscopy; Biotage for a generous donation of microwave process vials, which were used extensively during these studies; and the Department of Defense and the Hertz Foundation for pre-doctoral fellowships (D.P.O.). Financial support for this work was provided by The Scripps Research Institute, Amgen, Dupont, Eli Lilly, GlaxoSmithKline, Roche, the Searle Scholarship Fund, NIH/NIGMS (GM-073949 to P.S.B), the National Science Foundation (research grant CHE-0240203 to K.N.H), and IGERT (a (MCTP)-DGE-0114443 fellowship to B.H.N.).

Publication History

  1. Issue published online: 8 JUN 2006
  2. Article first published online: 16 MAY 2006
  3. Manuscript Received: 7 FEB 2006

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Keywords:

  • alkaloids;
  • biosynthesis;
  • computational chemistry;
  • natural products;
  • rearrangement

Graphical Abstract

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Naturally radical: The microwave-induced rearrangement of sceptrin to natural products ageliferin and nagelamide E results in approximately the same ratio as they are isolated from natural sources. Computational investigations show that the vinylcyclobutane–cyclohexene rearrangement occurs via diradical intermediates and support the involvement of this rearrangement in the biosynthesis of the natural products.

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