Total Synthesis of Palau’amine

Authors

  • Ian B. Seiple,

    1. Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA, 92037 (USA), Fax: (+1) 858-784-7375
    Search for more papers by this author
    • These authors contributed equally to this paper.

  • Shun Su Dr.,

    1. Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA, 92037 (USA), Fax: (+1) 858-784-7375
    Search for more papers by this author
    • These authors contributed equally to this paper.

  • Ian S. Young Dr.,

    1. Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA, 92037 (USA), Fax: (+1) 858-784-7375
    Search for more papers by this author
  • Chad A. Lewis Dr.,

    1. Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA, 92037 (USA), Fax: (+1) 858-784-7375
    Search for more papers by this author
  • Junichiro Yamaguchi Prof. Dr.,

    1. Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA, 92037 (USA), Fax: (+1) 858-784-7375
    Search for more papers by this author
  • Phil S. Baran Prof. Dr.

    1. Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA, 92037 (USA), Fax: (+1) 858-784-7375
    Search for more papers by this author

  • We are grateful to Lars Jørgensen and Dr. Tanja Gaich for technical assistance. We thank Prof. Dr. M. Köck for helpful discussions. Financial support for this work was provided by the NIH/NIGMS (GM-073949), Amgen, Bristol-Myers Squibb (postdoctoral fellowship to S.S.), the Japan Society for the Promotion of Science (JSPS) for a postdoctoral fellowship to J.Y., the Natural Sciences and Engineering Research Council of Canada (NSERC) for a postdoctoral fellowship to I.S.Y., the Canadian Institutes of Health Research (CIHR) for a postdoctoral fellowship to C.A.L., and the NSF for a predoctoral fellowship to I.B.S.

Abstract

original image

Worth the wait: The long anticipated total synthesis of palau'amine has been accomplished by a route featuring highly chemoselective transformations, cascade reactions, and a remarkable transannular cyclization to secure the unprecedented trans-5,5 ring junction (shown in red).

Ancillary