Total Synthesis of Antibacterial Macrolide Sorangiolide A

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Natural Product Synthesis

Background:

• Antibacterial macrolides are crucial in combating bacterial infections.
• Sorangiolide A is a natural product with potential antibacterial properties.
• Efficient synthetic routes are needed for the study and application of such compounds.

Purpose of the Study:

• To develop a novel, convergent, and asymmetric total synthesis of sorangiolide A.
• To explore the structural and conformational properties of sorangiolide A in solution.

Main Methods:

• Utilized a convergent synthetic strategy.
• Employed key reactions including Krische iridium-catalyzed anti-diastereoselective carbonyl crotylation, Crimmins acetate aldol, Yamaguchi esterification, Julia-Kocienski olefination, Horner-Wadsworth-Emmons olefination, and ring-closing metathesis.
• Investigated the 13C{1H} NMR signals of C1 and C2 centers to understand solution-phase behavior.

Main Results:

• Successfully achieved the first asymmetric total synthesis of sorangiolide A.
• Identified specific synthetic methodologies enabling the construction of the macrolide core.
• Provided insights into the low intensity of 13C{1H} NMR signals at C1 and C2.

Conclusions:

• The developed synthetic route is efficient and scalable for producing sorangiolide A.
• The study elucidates potential solution-phase conformations of sorangiolide A.
• This work provides a foundation for further investigation into the biological activity of sorangiolide A.