Tetranortriterpene Synthesis

  • ChemPubSoc Europe Logo
  • Author: Andrei Dragan
  • Published Date: 25 March 2017
  • Source / Publisher: Asian Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Tetranortriterpene Synthesis

The naturally occurring tetranortriterpene gedunin (pictured) has a wide range of important biological properties (antimalarial, insecticidal, anti-cancer). Although this molecule has received substantial research attention, there has not been a de novo synthesis since it was first isolated in 1960.

Craig Williams, University of Queensland, St. Lucia, Australia, and colleagues have discovered the first synthetic route to the complete ABC ring system of gedunin. Key transformations in this sequence include: (i) consecutive stereoselective annulation reactions, (ii) a Pd-catalyzed epoxide reduction which relies on triethylamine for the generation of a reactive Pd-imino species, and (iii) the protection of a β-hydroxy ketone as a 3-alkoxy dioxane, which proved resistant to dissolving metal reduction, amide and hydride bases, and oxidation with H2O2, but was cleaved using mildly acidic conditions.

The researchers successfully synthesized the fully decorated ABC ring system of gedunin, incorporating the 7-α-acetoxy residue, which until now lacked a versatile protocol. These results could help to further develop medicinal chemistry based on this biologically important molecule.


Article Views: 1400

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

Bookmark and Share

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more


ChemistryViews.org on Facebook

ChemistryViews.org on Twitter ChemistryViews.org on YouTube ChemistryViews.org on LinkedIn Sign up for our free newsletter

A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH