Jump to main content
Jump to site search


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

Author affiliations

Abstract

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.

Graphical abstract: Metamorphosis of cycloalkenes for the divergent total synthesis of polycyclic indole alkaloids

Back to tab navigation

Publication details

The article was received on 01 Jun 2018 and first published on 20 Aug 2018


Article type: Tutorial Review
DOI: 10.1039/C8CS00454D
Citation: Chem. Soc. Rev., 2018, Advance Article
  •   Request permissions

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

    Z. Xu, Q. Wang and J. Zhu, Chem. Soc. Rev., 2018, Advance Article , DOI: 10.1039/C8CS00454D

Search articles by author

Spotlight

Advertisements