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Metamorphosis of cycloalkenes for the divergent total synthesis of polycyclic indole alkaloids.
Journal article

Metamorphosis of cycloalkenes for the divergent total synthesis of polycyclic indole alkaloids.

  • Xu Z Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH5304, CH-1015 Lausanne, Switzerland. jieping.zhu@epfl.ch.
  • Wang Q
  • Zhu J
  • 2018-08-21
Published in:
  • Chemical Society reviews. - 2018
English From tryptamine and secologanine, nature generates monoterpene indole alkaloids with an unprecedented level of skeletal diversity through a 'couple-divert' sequence. Intrigued by this biosynthetic machinery, new strategies and tactics to access skeletally distinct natural products are continuously emerging. In this Tutorial Review, we'll present a simplified view of nature's logic for biosynthesis and the representative strategies and tactics developed for the divergent total synthesis of monoterpene indole alkaloids. Our group has been developing a 'couple-divert' approach with the strategic use of cycloalkene as a pluripotent motif in the synthetic design and has developed an integrated oxidation/reduction/cyclization (iORC) sequence for transforming functionalized cycloalkenes, easily available by a variety of cross-coupling reactions, to skeletally diverse natural products. The integration of controlled regio-, chemo- and stereo-selective cyclization and heteroannulation reactions into these domino sequences will be highlighted.
Language
  • English
Open access status
closed
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Persistent URL
https://sonar.ch/global/documents/204587
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