Cut and sew: benzofuran-ring-opening enabled cyclopentenone ring formation

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Catalysis

Background:

• Cyclopentenones are important structural motifs in natural products and pharmaceuticals.
• Existing synthetic routes often require harsh conditions or specialized reagents.
• Benzofuran derivatives are versatile synthetic intermediates.

Purpose of the Study:

• To develop a facile and efficient synthetic strategy for fully substituted cyclopentenones.
• To explore a novel benzofuran-ring-opening reaction as a key step.
• To achieve high yields and diastereoselectivities in the synthesis of complex cyclopentenones.

Main Methods:

• Acid-catalyzed cascade reaction.
• Benzofuran endocyclic C2-O bond cleavage.
• Synthesis of fully substituted cyclopentenones without transition metal catalysts.

Main Results:

• Demonstrated a facile approach to fully substituted cyclopentenones.
• Achieved unprecedented benzofuran-ring-opening under mild conditions.
• Obtained excellent yields and diastereoselectivities in the cascade process.

Conclusions:

• A novel synthetic strategy for complex cyclopentenones has been established.
• The developed method offers an efficient and catalyst-free benzofuran-ring-opening.
• This approach provides a valuable new tool for organic synthesis.