Synthesis of montroumarin

Area of Science:

• Organic Chemistry
• Natural Product Synthesis
• Medicinal Chemistry

Background:

• Montrouziera sphaeroidea is a plant source of bioactive natural products.
• Montroumarin is a dihydroisocoumarin with potential biological activities.
• Stereoselective synthesis is crucial for obtaining enantiomerically pure compounds.

Purpose of the Study:

• To develop a simple stereoselective synthesis of montroumarin.
• To evaluate the antifungal activity of synthesized compounds.

Main Methods:

• Condensation of benzoyl chloride with 3,5-dimethoxyhomophthalic acid.
• Saponification and esterification to form a keto ester.
• Enantioselective reduction using baker's yeast.
• Demethylation to yield montroumarin.

Main Results:

• Synthesis of 6,8-dimethoxy-3-phenylisocoumarin and subsequent keto ester.
• Successful enantioselective reduction to (3S)-6,8-dimethoxy-3-phenyl-3,4-dihydroisocoumarin with good enantioselectivity.
• Demethylation to afford montroumarin.
• In vitro antifungal activity assessment of synthesized compounds.

Conclusions:

• A straightforward stereoselective synthesis of montroumarin was established.
• The synthesized compounds provide a basis for further investigation of their biological properties.
• This synthetic route enables access to enantiomerically pure montroumarin for medicinal chemistry studies.