Total synthesis of leustroducsin B

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Medicinal Chemistry

Background:

• Leustroducsin B is a natural product known for its diverse biological activities.
• Efficient and stereoselective synthesis of complex natural products is crucial for biological evaluation and drug discovery.

Purpose of the Study:

• To achieve a convergent total synthesis of leustroducsin B.
• To develop novel synthetic methodologies applicable to complex, densely functionalized molecules.

Main Methods:

• Lipase-mediated desymmetrization of a meso-diol to construct the C8 stereocenter with high enantioselectivity (90.2% ee).
• Stereoselective formation of the C9-C11 anti-diol moiety using an alkynylzinc reagent addition.
• Development and application of a novel p-silyloxybenzylidene diol protecting group.

Main Results:

• Successful convergent total synthesis of leustroducsin B.
• Efficient construction of key stereocenters and functional groups.
• Demonstration of the utility of the new diol protecting group, removable under mild acidic conditions.

Conclusions:

• The developed synthetic route provides access to leustroducsin B and showcases innovative chemical strategies.
• The new protecting group offers a valuable tool for the synthesis of complex molecules with multiple hydroxyl groups.