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Synthesis 1999; 1999(4): 525-558
DOI: 10.1055/s-1999-3435
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The Lactone Concept: An Efficient Pathway to Axially Chiral Natural Products and Useful Reagents

Gerhard Bringmann* , Matthias Breuning, Stefan Tasler
  • *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 1999 (online)

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A highly efficient concept for the stereoselective synthesis of axially chiral biaryl target molecules is presented: the atroposelective ring cleavage of configurationally unstable lactone-bridged biaryls. The method has almost no restrictions concerning the substitution pattern, works even for substrates with high steric hindrance at the ortho-position(s) of the axis, and allows the optional, atropo-divergent preparation of each atropisomer from the same biaryl lactone precursor and a recycling of the undesired minor product in the sense of a chiral economy. A brpad series of successful application in natural product and ligand syntheses underlines the high value of the method.

axial chirality - biaryl natural products - biaryl ligands and reagents - atropo-divergent synthesis - lactone-bridged biaryls