Concise Total Synthesis of (+)-Paniculatine

  • Author: ChemistryViews.org
  • Published: 13 May 2019
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Advanced Synthesis & Catalysis/Wiley-VCH
thumbnail image: Concise Total Synthesis of (+)-Paniculatine

Lycopodium alkaloids are a class of natural products with high structural diversity and biological activities. Lycopodium is a genus of clubmosses from which these compounds were isolated. (+)-Paniculatine (pictured) from Lycopodium paniculatum has a tetracyclic framework with seven stereogenic centers. While there are several total syntheses for (+)-paniculatine and similar alkaloids, they involve between 25 and 45 steps.


Fayang G. Qiu, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou, and University of the Chinese Academy of Sciences, Beijing, and colleagues have developed a concise total synthesis of (+)-paniculatine. The team started from two known intermediates: a thioether-substituted cyclohexanone and an iodine-substituted cyclic enone. These two compounds were coupled, allylated, and converted to a iodohydrin. Then the third ring was closed using a SN2 cyclization. The tetracyclic system was completed using an intramolecular Michael addition.


The synthesis has ten steps in total and gives an overall yield of 12 %. According to the researchers, the same strategy could be used for the synthesis of two related natural products, (−)-magellanine and (+)-magellaninone.


 

 

Article Views: 1221

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


CONNECT:

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