Related Experiment Video
Updated: Nov 15, 2025

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
Total Synthesis of the Meroterpenoid Manginoid A as Fueled by a Challenging Pinacol Coupling and Bicycle-forming
Yu-An Zhang1, Amanda Milkovits1, Valay Agarawal1
1Department of Chemistry, University of Chicago, 5735 S. Ellis Avenue, Chicago, IL, 60637, USA.
Abstract:
The manginoids are a unique collection of bioactive natural products whose structures fuse an oxa-bridged spirocyclohexanedione with a heavily substituted trans-hydrindane framework. Herein, we show that such architectures can be accessed through a strategy combining a challenging pinacol coupling and bicycle-forming etherification with several additional chemo- and regioselective reactions. The success of these key events proved to be highly substrate and condition specific, affording insights for their application to other targets. As a result, not only has a 19-step total synthesis of manginoid A been achieved, but a potential roadmap to access other members of the family and related natural products has also been identified.
Related Concept Videos
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Oxymercuration-Reduction of Alkenes
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

