A facile and highly atom-economic approach to biaryl-containing medium-ring bislactones

Area of Science:

• Organic Chemistry
• Photochemistry
• Synthetic Methodology

Background:

• Medium-ring bislactones are valuable structural motifs found in various natural products.
• Efficient synthetic routes to complex bislactone structures remain a challenge in organic synthesis.

Purpose of the Study:

• To develop a facile and efficient method for the synthesis of biaryl containing medium-ring bislactones.
• To explore the utility of sequential photocycloaddition-photooxidation reactions in constructing complex molecular architectures.

Main Methods:

• The study employed readily available phenanthrenequinone and various alkenes as starting materials.
• Sequential photocycloaddition followed by photooxidation reactions were utilized to construct the bislactone framework.
• Reaction conditions were optimized to achieve good yields and diastereoselectivity.

Main Results:

• Biaryl containing medium-ring bislactones were successfully synthesized with good overall yields.
• The reactions exhibited good diastereoselectivity, leading to the preferential formation of specific stereoisomers.
• The synthetic strategy proved to be versatile, accommodating a range of alkene substrates.

Conclusions:

• The developed sequential photocycloaddition-photooxidation strategy provides an accessible route to biaryl medium-ring bislactones.
• This method offers a valuable tool for synthetic chemists seeking to access complex lactone structures.
• The efficiency and selectivity of the reactions highlight the potential of photochemistry in constructing intricate organic molecules.