Total synthesis of ripostatin A.
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.
Helmholtz Centre for Infection Research, Inhoffenstr. 7, D-38124 Braunschweig, Germany.
Wufeng
W
Tang
Evgeny V
EV
Prusov
D002384:Catalysis; D003500:Cyclization; D012321:DNA-Directed RNA Polymerases / Q000037:antagonists & inhibitors*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D007783:Lactones; C096600:ripostatin A; D012321:DNA-Directed RNA Polymerases