The Total Synthesis of the Oxopolyene Macrolide RK-397

Authors

  • Mark J. Mitton-Fry Dr.,

    1. Department of Chemistry and Biochemistry, University of Colorado, 215 UCB, Boulder, CO 80309-0215, USA, Fax: (+1) 303-492-0439
    2. Current address: Pfizer Global Research and Development, Groton, CT 06340, USA
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  • Aaron J. Cullen,

    1. Department of Chemistry and Biochemistry, University of Colorado, 215 UCB, Boulder, CO 80309-0215, USA, Fax: (+1) 303-492-0439
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  • Tarek Sammakia Prof. Dr.

    1. Department of Chemistry and Biochemistry, University of Colorado, 215 UCB, Boulder, CO 80309-0215, USA, Fax: (+1) 303-492-0439
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  • This work was supported by a grant from the National Institutes of Health (GM48498). We wish to thank Prof. H. Osada for providing NMR spectra of RK-397. M.J.M. gratefully acknowledges the National Science Foundation and also Pharmacia and Upjohn for fellowships.

Abstract

original image

It works both ways: The convergent total synthesis of the oxopolyene macrolide RK-397 utilizes remote asymmetric induction and a two-directional chain synthesis to prepare the polyol portion of the molecule, as well as a cross-metathesis reaction of a trienal with a terminal alkene to append the polyene to the polyol.

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