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Synthesis 2000; 2000(3): 383-388
DOI: 10.1055/s-2000-6340
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A New Central Binaphthalene Building Block for Michellamine Syntheses

Gerhard Bringmann* , Thomas Ortmann, Doris Feineis, Eva-Maria Peters, Karl Peters
  • *Institut für Organische Chemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany; Fax +49 (9 31) 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 synthesis of a new, suitably protected and activated binaphthalene building block representing the central structural element of all known natural dimeric naphthylisoquinoline alkaloids, is described. This functionalized fragment possesses organometallically robust O-isopropyl (instead of O-acetyl) protecting groups and bromo (instead of trifluoromethanesulfonyloxy) activation at the scheduled coupling positions. Starting from a biphenyl intermediate, the construction of the two `outer' naphthalene rings has been achieved by a Wittig reaction → cyclization sequence.

michellamines - binaphthalene building blocks - Wittig reaction - biaryls - natural products - protecting groups - cyclizations