Total Synthesis of (+)-Steenkrotin A

  • Author: Shaun Scally
  • Published Date: 22 December 2015
  • Source / Publisher: Chemistry – A European Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Total Synthesis of (+)-Steenkrotin A

Related Societies

Isolation studies targeting Croton plants have yielded a wealth of structurally intriguing and biologically active natural products. Recent efforts aimed at identifying potentially medicinal diterpenoid compounds extracted from the leaves of Croton Steenkampianus resulted in the isolation of two new compounds with moderate antiplasmodial activities, which were named (+)-steenkrotins A and B.

Hanfeng Ding and co-workers, Zhejiang University, Hangzhou, China, have accomplished the first enantioselective total synthesis of (+)-steenkrotin A (pictured) in 18 steps and 4.2 % overall yield, starting from an easily accessible chiral cycloheptenone. The strategy includes three key ring formations: 1) a Rh-catalyzed O–H bond insertion followed by an intramolecular carbonyl-ene reaction to construct the tetrahydrofuran subunit; 2) two sequential SmI2-mediated Ueno-Stork and ketyl-olefin cyclizations to build up the [5,7]spirobicyclic skeleton; and 3) a cascade intramolecular aldol condensation/vinylogous retro-aldol/aldol reaction to forge the final six-membered ring with inversion of the relative configuration at the C7 position.

The described synthesis established the absolute configuration of (+)-steenkrotin A by stepwise construction of the stereocenters. The team hopes that the methodologies and strategies employed will find further application in the synthesis of other complex natural products.


Article Views: 4008

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, please contact us first for permission and consult our permisson 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