Total synthesis of racemic thieno[3,2-f]thiochromene tricarboxylate, a luciferin from marine polychaete Odontosyllis undecimdonta
The luciferin of the bioluminescent system of O. undecimdonta, which emits green-blue light, is an unusual heterocycle with previously unknown thieno[3,2-f]thiochromene skeleton. Despite numerous methods for the synthesis of benzothiophenes and thiochromenes, no synthetic approaches to thieno[3,2-f]thiochromenes have been proposed so far. The researchers from the Laboratory of Chemistry of Metabolic Pathways developed a convergent synthetic pathway to thieno[3,2-f]thiochromene tricarboxylate via cascade reactions with the use of bifunctional reagents, which afforded the structural confirmation of Odontosyllis undecimdonta luciferin and opened the route to other thieno[3,2-f]thiochromenes that were not accessible via known synthetic methods. The research was published in Organic Letters. Learn more
june 28, 2023