Total Synthesis of (±)-Axinellamines A and B

Authors

  • Daniel P. O'Malley,

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

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

  • 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
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    • Both authors contributed equally to this paper.

  • 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
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  • We thank Prof. R. J. Quinn for a sample of authentic 1. Financial support for this work was provided by the NIH/NIGMS (GM-073949), Bristol–Myers Squibb, Eli Lilly, Merck, 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., and the U.S. Department of Defense and the Hertz Foundation for predoctoral fellowships to D.P.O.

Abstract

original image

Chemoselektiv per Entwurf: Die erste Totalsynthese von Mitgliedern der Axinellamin-/Palau'amin-/Massadin-Klasse der Pyrrolimidazol-Alkaloide besticht durch ungewöhnliche Transformationen an vollständig ungeschützten Polyamino- und hydroxylierten Substraten und umfasst außerdem eine neue Methode für chemoselektive Oxidationen.

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