Total Synthesis of Racemic Thieno[3,2- f ]thiochromene Tricarboxylate, a Luciferin from Marine Polychaeta Odontosyllis undecimdonta .

Autor: Bolt YV; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia., Dubinnyi MA; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia.; Moscow Institute of Physics and Technology, Dolgoprudny 141701, Russia., Litvinenko VV; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia., Kotlobay AA; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia., Belozerova OA; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia., Zagitova RI; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia., Shmygarev VI; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia., Yatskin ON; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia., Guglya EB; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia.; Pirogov Russian National Research Medical University, Moscow 117997, Russia., Kublitski VS; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia., Baranov MS; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia.; Pirogov Russian National Research Medical University, Moscow 117997, Russia., Yampolsky IV; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia.; Pirogov Russian National Research Medical University, Moscow 117997, Russia.; Planta LLC, Moscow 109507, Russia., Kaskova ZM; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia.; Pirogov Russian National Research Medical University, Moscow 117997, Russia., Tsarkova AS; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia.; Pirogov Russian National Research Medical University, Moscow 117997, Russia.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2023 Jul 07; Vol. 25 (26), pp. 4892-4897. Date of Electronic Publication: 2023 Jun 27.
DOI: 10.1021/acs.orglett.3c01696
Abstrakt: We report the first total synthesis of racemic Odontosyllis undecimdonta luciferin, a thieno[3,2- f ]thiochromene tricarboxylate comprising a 6-6-5-fused tricyclic skeleton with three sulfur atoms in different electronic states. The key transformation is based on tandem condensation of bifunctional thiol-phosphonate, obtained from dimethyl acetylene dicarboxylate, with benzothiophene-6,7-quinone. The presented convergent approach provides the synthesis of the target compound with a previously unreported fused heterocyclic core in 11 steps, thus allowing for unambiguous confirmation of the chemical structure of Odontosyllis luciferin by 2D-NMR spectroscopy.
Databáze: MEDLINE
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