Total Synthesis of (+)-Heilonine

  • Author: ChemistryViews
  • Published: 30 September 2021
  • Copyright: Wiley-VCH GmbH
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Total Synthesis of (+)-Heilonine

Alkaloid natural products can have a variety of biological activities. Heilonine (pictured), for example, is a hexacyclic alkaloid with a challenging structure for total synthesis. Known syntheses of similar compounds require a large number of steps.


Kyle J. Cassaidy and Viresh H. Rawal, University of Chicago, IL, USA, have performed a convergent enantioselective total synthesis of (+)-heilonine. The team's strategy involves a transition-metal-catalyzed [2+2+2] cycloisomerization reaction, which creates three new C–C bonds in one step. The researchers first enantioselectively synthesized a diyne fragment that contains the A and B rings of the target compound. The fragment was connected to a propargyl-substituted piperidinone that contains the F ring. An intramolecular [2+2+2] cycloisomerization reaction using Wilkinson's catalyst was then used to close the C, D, and E rings in one step. With the carbon skeleton completed, further functionalization steps gave the desired product.


The team obtained (+)-heilonine in 21 steps (starting from ethyl vinyl ketone). According to the researchers, the convergent, modular approach could also be useful to access related natural compounds and other analogs. This could allow studies of their biological activities.


 

 

Article Views: 2691

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

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission and consult our permission guidance prior to making your request

Follow on Facebook Follow on Twitter Follow on YouTube Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH