Total Synthesis of Antibacterial Macrolide Sorangiolide A

A convergent route for the asymmetric total synthesis of antibacterial macrolide sorangiolide A has been developed for the first time. The key feature of this synthesis includes Krische iridium-catalyzed anti-diastereoselective carbonyl crotylation, Crimmins acetate aldol, Yamaguchi esterification, Julia-Kocienski olefination, Horner-Wadsworth-Emmons olefination, and ring-closing metathesis. The origin of the low intensity of the C-13{H-1} NMR signals of the C1 and C2 centers of the natural product has been investigated, disclosing possible forms of existence for the natural product in the solution phase.

Automated summary

A convergent route for the asymmetric total synthesis of antibacterial macrolide sorangiolide A has been developed, incorporating key reactions to address the low intensity of C1 and C2 center NMR signals and revealing the possible forms of existence for the natural product in solution.