2012/08/23 by Wufeng Tang, Evgeny V. Prusov · 1 citation
Biochemistry, Genetics and Molecular Biology · Chemistry · #Acetal #Biochemistry #Carbohydrate Chemistry and Synthesis #Catalysis #Chemical Synthesis and Analysis #Chemistry #Combinatorial chemistry #Metathesis #Organic chemistry #Ring (chemistry) #Ring-closing metathesis #Salt metathesis reaction #Sequence (biology) #Stereochemistry #Stille reaction #Synthetic Organic Chemistry Methods #Total synthesis
paper · doi:10.1021/ol302219x
openalex publication_date 2012/08/23 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/17
The first total synthesis of the bacterial RNA-polymerase inhibitor ripostatin A (1) was achieved. The route utilizes a cyclic methyl acetal intermediate and a sequence of a double Stille cross-coupling reaction followed by a ring-closing metathesis for the construction of the macrolactone ring. Additionally, an unprecedented formation of the 4-methoxy substituted tetrahydropyrans was observed during the acid catalyzed acetalization of the β,δ-dihydroxyketone.