Total Synthesis of Racemic Thieno[3,2-f]thiochromene Tricarboxylate, a Luciferin from Marine Polychaeta Odontosyllis undecimdonta
Yaroslav V Bolt
1
,
Maxim A Dubinnyi
1, 2
,
Veronika V. Litvinenko
1
,
Alexey A Kotlobay
1
,
Vladimir I. Shmygarev
1
,
Oleg N Yatskin
1
,
Elena B Guglya
1, 3
,
Vadim S Kublitski
1
,
Mikhail Baranov
1, 3
,
Ilia V. Yampolsky
1, 3, 4
,
Zinaida M Osipova
1, 3
,
A. S. Tsarkova
1, 3
4
Planta LLC, Moscow 109507, Russia
|
Publication type: Journal Article
Publication date: 2023-06-27
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
37366567
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
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.
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Bolt Y. V. et al. Total Synthesis of Racemic Thieno[3,2-f]thiochromene Tricarboxylate, a Luciferin from Marine Polychaeta Odontosyllis undecimdonta // Organic Letters. 2023. Vol. 25. No. 26. pp. 4892-4897.
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Bolt Y. V., Dubinnyi M. A., Litvinenko V. V., Kotlobay A. A., Belozerova O. A., Zagitova R. I., Shmygarev V. I., Yatskin O. N., Guglya E. B., Kublitski V. S., Baranov M., Yampolsky I. V., Osipova Z. M., Tsarkova A. S. Total Synthesis of Racemic Thieno[3,2-f]thiochromene Tricarboxylate, a Luciferin from Marine Polychaeta Odontosyllis undecimdonta // Organic Letters. 2023. Vol. 25. No. 26. pp. 4892-4897.
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TY - JOUR
DO - 10.1021/acs.orglett.3c01696
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.3c01696
TI - Total Synthesis of Racemic Thieno[3,2-f]thiochromene Tricarboxylate, a Luciferin from Marine Polychaeta Odontosyllis undecimdonta
T2 - Organic Letters
AU - Bolt, Yaroslav V
AU - Dubinnyi, Maxim A
AU - Litvinenko, Veronika V.
AU - Kotlobay, Alexey A
AU - Belozerova, Olga A
AU - Zagitova, Renata I
AU - Shmygarev, Vladimir I.
AU - Yatskin, Oleg N
AU - Guglya, Elena B
AU - Kublitski, Vadim S
AU - Baranov, Mikhail
AU - Yampolsky, Ilia V.
AU - Osipova, Zinaida M
AU - Tsarkova, A. S.
PY - 2023
DA - 2023/06/27
PB - American Chemical Society (ACS)
SP - 4892-4897
IS - 26
VL - 25
PMID - 37366567
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2023_Bolt,
author = {Yaroslav V Bolt and Maxim A Dubinnyi and Veronika V. Litvinenko and Alexey A Kotlobay and Olga A Belozerova and Renata I Zagitova and Vladimir I. Shmygarev and Oleg N Yatskin and Elena B Guglya and Vadim S Kublitski and Mikhail Baranov and Ilia V. Yampolsky and Zinaida M Osipova and A. S. Tsarkova},
title = {Total Synthesis of Racemic Thieno[3,2-f]thiochromene Tricarboxylate, a Luciferin from Marine Polychaeta Odontosyllis undecimdonta},
journal = {Organic Letters},
year = {2023},
volume = {25},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.3c01696},
number = {26},
pages = {4892--4897},
doi = {10.1021/acs.orglett.3c01696}
}
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Bolt, Yaroslav V., et al. “Total Synthesis of Racemic Thieno[3,2-f]thiochromene Tricarboxylate, a Luciferin from Marine Polychaeta Odontosyllis undecimdonta.” Organic Letters, vol. 25, no. 26, Jun. 2023, pp. 4892-4897. https://pubs.acs.org/doi/10.1021/acs.orglett.3c01696.