Total synthesis of racemic thieno[3,2-f]thiochromene tricarboxylate, a luciferin from marine polychaete Odontosyllis undecimdonta
The researchers from the Laboratory of Chemistry of Metabolic Pathways in collaboration with colleagues from other department of IBCh RAS conducted the total synthesis of luciferin from marine polychaete Odontosyllis undecimdonta, a heterocyclic compound with a previously unknown skeleton. The research was published in Organic Letters.
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.