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Total Synthesis of Phorbazole B.
Yngve Guttormsen1, Magnus E Fairhurst2, Sunil K Pandey2
1Department of Chemistry, UiT The Arctic University of Norway, Hansine Hansens veg 54, 9037 Tromsø, Norway.
Molecules (Basel, Switzerland)
|October 24, 2020
Summary
Researchers synthesized trichlorinated phorbazole B from a marine sponge using late-stage electrophilic chlorination. Attempts to create phorbazoles A and C with specific chlorination patterns were unsuccessful due to synthetic challenges.
Area of Science:
- Marine natural products chemistry
- Organic synthesis
- Medicinal chemistry
Background:
- Phorbazoles are marine sponge-derived polychlorinated heterocyclic metabolites.
- Several phorbazoles exhibit anticancer activity, highlighting their therapeutic potential.
Purpose of the Study:
- To develop a synthetic route for trichlorinated phorbazole B.
- To investigate the feasibility of synthesizing phorbazoles A and C.
Main Methods:
- Late-stage electrophilic chlorination of an oxazole precursor.
- Protection of the oxazole 4-position with iodine.
- Complete chlorination of pyrrole positions.
- Structure elucidation using advanced NMR techniques (NOESY/ROESY, 1,1-ADEQUATE, CLIP-HSQMBC).
Main Results:
- Successful synthesis of trichlorinated phorbazole B.
- Unsuccessful synthesis of phorbazoles A and C due to inability to achieve the desired 3,4-dichlorination pattern on the pyrrole ring.
- Characterization of intermediates and products confirmed by NMR spectroscopy.
Conclusions:
- A viable synthetic strategy for phorbazole B was established.
- The synthesis of phorbazoles A and C presents significant regioselectivity challenges.
- Advanced NMR methods are crucial for structural determination of complex chlorinated heterocycles.
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