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Synthesis 2000; 2000(13): 1843-1847
DOI: 10.1055/s-2000-8236
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One-Step Oxidative Dimerization of Genuine, Unprotected Naphthylisoquinolines Alkaloids to Give Michellamines and Other Bioactive Quateraryls

Gerhard Bringmann* , Wael Saeb, Jan Mies, Kim Messer, Michael Wohlfarth, Reto Brun
  • *Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany; Fax +49(931)8 88 47 55; E-mail: bringman@chemie.uni-wuerzburg.de
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Publication Date:
31 December 2000 (online)

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The first one-step oxidative dimerization of monomeric naphthylisoquinoline alkaloids, using lead tetraacetate or phenyliodine(III) bis(trifluoroacetate) is described, thus avoiding previous 5- or 3-step reaction sequences involving protection, reduction, and deprotection reactions. The method is exemplified for the first nonenzymic direct preparation of michellamines A (1a) and C (1b) from korupensamines A (3a) and B (3b), respectively, and for the synthesis of the new quateraryl jozimine D (2), the unnatural dimer of natural dioncophylline B (5).

lead tetraacetate - phenyliodine(III) bis(trifluoroacetate) - michellamines - jozimine D - naphthylisoquinoline alkaloids - oxidative phenolic coupling - biaryls

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