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Total Synthesis of (+)-Panacene.
Neanne Alnafta1, Johannes P Schmidt1, Caroline L Nesbitt1
1School of Chemistry, The University of Sydney , Sydney, New South Wales 2006, Australia.
Organic Letters
|December 17, 2016
Summary
Researchers achieved the first total synthesis of the marine bromoallene (+)-panacene. This enantioselective synthesis utilized Noyori transfer hydrogenation for dynamic kinetic resolution to establish absolute stereochemistry.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
Background:
- Marine natural products possess unique chemical structures.
- (+)-Panacene is a marine bromoallene with potential biological significance.
- Total synthesis provides access to complex natural products for further study.
Purpose of the Study:
- To achieve the first total synthesis of the naturally occurring enantiomer of (+)-panacene.
- To develop a concise and enantioselective synthetic route.
- To explore biomimetic strategies for constructing axially chiral allenes.
Main Methods:
- Enantioselective synthesis utilizing Noyori transfer hydrogenation for Dynamic Kinetic Resolution (DKR).
- Stereoselective Julia coupling to install a Z-configured enyne.
- Biomimetic construction of the bromoallene core.
Main Results:
- Successful synthesis of the first total synthesis of (+)-panacene.
- Establishment of the desired absolute stereochemistry via DKR.
- Efficient installation of the Z-enyne moiety and subsequent bromoallene formation.
Conclusions:
- A concise and enantioselective route to (+)-panacene has been established.
- The synthetic strategy highlights the utility of DKR and stereoselective coupling reactions.
- This work provides a foundation for exploring other complex marine natural products.
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