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Synthetic study toward tridachiapyrone B
Morgan Cormier1, Florian Hernvann1, Michaël De Paolis1
1COBRA, Normandie University, 76000 Rouen, France.
Beilstein Journal of Organic Chemistry
|January 11, 2023
Summary
This study presents a novel convergent synthesis for tridachiapyrone B. Key steps include desymmetrization and Robinson-type annulation to build the complex molecular skeleton efficiently.
Area of Science:
- Organic Synthesis
- Natural Product Chemistry
- Medicinal Chemistry
Background:
- Tridachiapyrone B is a marine natural product with potential biological activities.
- Efficient synthetic routes are crucial for further investigation and analog development.
Purpose of the Study:
- To develop a convergent synthetic strategy for the skeleton of tridachiapyrone B.
- To establish key reactions for constructing the core structure and side chain.
Main Methods:
- Desymmetrization of α,α'-dimethoxy-γ-pyrone to α-crotyl-α'-methoxy-γ-pyrone.
- Robinson-type annulation for quaternary carbon construction.
- Oxidative anionic oxy-Cope rearrangement for side chain installation.
Main Results:
- A one-step desymmetrization yielded a key intermediate.
- Successful construction of the 2,5-cyclohexadienone core via annulation.
- Demonstrated grafting of the simplified side chain using oxy-Cope rearrangement.
Conclusions:
- The developed convergent approach provides an efficient route to the tridachiapyrone B skeleton.
- The strategy highlights the utility of key transformations in complex molecule synthesis.
