Studies toward Providencin: The Furanyl-Cyclobutanol Segment
Simon M Spohr1, Alois Fürstner1
1Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim/Ruhr, Germany.
Organic Letters
|February 27, 2023
Summary
Researchers developed a new synthetic route for providencin, a complex furanocembranoid. The key step involved an iridium-catalyzed cycloaddition to create a crucial building block for this natural product.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Medicinal Chemistry
Background:
- Providencin, a furanocembranoid, is a challenging natural product target.
- Previous synthesis efforts have focused on less hydroxylated analogs like 17-deoxyprovidencin.
- A practical route to a fully hydroxylated providencin building block is needed.
Purpose of the Study:
- To develop a practical synthetic approach for a key hydroxylated building block of providencin.
- To utilize an iridium-catalyzed photosensitized intramolecular [2 + 2] cycloaddition as a pivotal reaction.
Main Methods:
- Iridium-catalyzed photosensitized intramolecular [2 + 2] cycloaddition.
- Synthesis of a hydroxylated furanocembranoid building block.
Main Results:
- A practical method for synthesizing a key hydroxylated building block was established.
- The synthesized intermediate could not be directly converted to providencin using a reported ring-closing metathesis (RCAM) approach.
- The building block holds potential for elaboration into providencin via alternative literature routes.
Conclusions:
- The study presents a viable strategy for accessing a crucial intermediate in providencin synthesis.
- The developed building block can be further modified to achieve the natural product.
- This work contributes to the total synthesis of complex furanocembranoids.
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