A convergent strategy for the pamamycin macrodiolides: Total synthesis of pamamycin-607, pamamycin-593, and pamamycin-621D precursors

S. Lanners, H. Norouzi-Arasi, X.J. Salom-Roig, Gilles Hanquet

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    Abstract

    A convergent total synthesis of pamamycin-607 (1), isolated from Streptomyces alboniger, was achieved by an E-Z isomerization of a tetrahydrofuran alkylidene and a regio- and diastereoselective solvent-dependent cyclo-CHBCl/EtN-mediated aldol reaction as the key steps. The second key step was extended to other ketones, opening the route to new pamamycin macrodiolides, for example, pamamycin-593 and pamamycin-621D. (Figure Presented) © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
    Original languageEnglish
    Pages (from-to)7086-7089
    Number of pages4
    JournalAngewandte Chemie. International edition
    Volume46
    Issue number37
    DOIs
    Publication statusPublished - 1 Jan 2007

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