Home / Publications / Triacetic acid lactone as a bioprivileged molecule in organic synthesis

Triacetic acid lactone as a bioprivileged molecule in organic synthesis

Dmitrii L'vovich Obydennov 1
Dmitrii L'vovich Obydennov
, 
Asmaa I El-Tantawy 1, 2
Asmaa I El-Tantawy
, 
Vyacheslav Yakovlevich Sosnovskikh 1
Vyacheslav Yakovlevich Sosnovskikh
10.1016/j.mencom.2019.01.001
Published 2018-12-28
Focus article , Volume 29, Issue 1, 1-10
30
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Obydennov D. L., El-Tantawy A. I., Sosnovskikh V. Y. Triacetic acid lactone as a bioprivileged molecule in organic synthesis // Mendeleev Communications. 2018. Vol. 29. No. 1. pp. 1-10.
GOST all authors (up to 50) Copy
Obydennov D. L., El-Tantawy A. I., Sosnovskikh V. Y. Triacetic acid lactone as a bioprivileged molecule in organic synthesis // Mendeleev Communications. 2018. Vol. 29. No. 1. pp. 1-10.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2019.01.001
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.01.001
TI - Triacetic acid lactone as a bioprivileged molecule in organic synthesis
T2 - Mendeleev Communications
AU - Obydennov, Dmitrii L'vovich
AU - El-Tantawy, Asmaa I
AU - Sosnovskikh, Vyacheslav Yakovlevich
PY - 2018
DA - 2018/12/28
PB - Mendeleev Communications
SP - 1-10
IS - 1
VL - 29
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2018_Obydennov,
author = {Dmitrii L'vovich Obydennov and Asmaa I El-Tantawy and Vyacheslav Yakovlevich Sosnovskikh},
title = {Triacetic acid lactone as a bioprivileged molecule in organic synthesis},
journal = {Mendeleev Communications},
year = {2018},
volume = {29},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.01.001},
number = {1},
pages = {1--10},
doi = {10.1016/j.mencom.2019.01.001}
}
MLA
Cite this
MLA Copy
Obydennov, Dmitrii L'vovich, et al. “Triacetic acid lactone as a bioprivileged molecule in organic synthesis.” Mendeleev Communications, vol. 29, no. 1, Dec. 2018, pp. 1-10. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.01.001.
Views / Downloads
1 / 8

Abstract

Major methods for the preparation of triacetic acid lactone and its application as a bioprivileged compound in the synthesis of various valuable materials are summarized. Due to its structural features, this lactone belongs to both pyrones and polyketides, which provides opportunities for its obtaining by chemical and biological methods. The presence of several electrophilic and nucleophilic centers in its molecule, as well as its capability of undergoing transformations with both preservation and opening of the ring, ensure its multiple reactivity. Reactions proceeding without the ring opening lead to substituted and fused pyrans, while the ring opening provides N-heterocycles and acyclic derivatives.

References

1.
Targeted chemical upgrading of lignocellulosic biomass to platform molecules
Luterbacher J.S., Martin Alonso D., Dumesic J.A.
Green Chemistry, 2014
2.
Biorenewable chemicals: Feedstocks, technologies and the conflict with food production
Bardhan S.K., Gupta S., Gorman M.E., Haider M.A.
Renewable and Sustainable Energy Reviews, 2015
3.
Wood-Derived Materials for Green Electronics, Biological Devices, and Energy Applications.
Zhu H., Luo W., Ciesielski P.N., Fang Z., Zhu J.Y., Henriksson G., Himmel M.E., Hu L.
Chemical Reviews, 2016
5.
Chernysheva D.V., Klushin V.A., Zubenko A.F., Pudova L.S., Kravchenko O.A., Chernyshev V.M., Smirnova N.V.
Mendeleev Communications, 2018
6.
Biosynthesis of α-pyrones
Schäberle T.F.
Beilstein Journal of Organic Chemistry, 2016
8.
ZIRAK M., EFTEKHARI-SIS B.
Turkish Journal of Chemistry, 2015
10.
Conversion of secondary furfuryl alcohols and isomaltol into maltol and related .gamma.-pyrones
Weeks P.D., Brennan T.M., Brannegan D.P., Kuhla D.E., Elliott M.L., Watson H.A., Wlodecki B., Breitenbach R.
Journal of Organic Chemistry, 1980
11.
Dehydroacetic Acid, Triacetic Acid Lactone, and Related Pyrones
Moreno-Mañas M., Pleixats R.
Advances in Heterocyclic Chemistry, 1992
12.
Bioprivileged molecules: creating value from biomass
Shanks B.H., Keeling P.L.
Green Chemistry, 2017
13.
Coupling chemical and biological catalysis: a flexible paradigm for producing biobased chemicals
Schwartz T.J., Shanks B.H., Dumesic J.A.
Current Opinion in Biotechnology, 2016
15.
Synthesis of novel 5,6-dehydrokawain analogs as osteogenic inducers and their action mechanisms
Kumagai M., Nishikawa K., Mishima T., Yoshida I., Ide M., Koizumi K., Nakamura M., Morimoto Y.
Bioorganic and Medicinal Chemistry Letters, 2017
16.
Synthesis, antitumor activity, and mechanism of action of 6-acrylic phenethyl ester-2-pyranone derivatives
Fang S., Chen L., Yu M., Cheng B., Lin Y., Morris-Natschke S.L., Lee K., Gu Q., Xu J.
Organic and Biomolecular Chemistry, 2015
18.
10.1016/j.mencom.2019.01.001_bib0040
Fadel
ARKIVOC, 2011
19.
10.1016/j.mencom.2019.01.001_sbref0045a
Collie
J. Chem. Soc., 1891
20.
DEHYDROACETIC ACID
Organic Syntheses, 1940
21.
858. Heterocyclic syntheses with malonyl chloride. Part VIII. Hydroxypyrones from 1,3-diketones
Butt M.A., Elvidge J.A.
Journal of the Chemical Society (Resumed), 1963
22.
Antitumor agents 287. Substituted 4-amino-2H-pyran-2-one (APO) analogs reveal a new scaffold from neo-tanshinlactone with in vitro anticancer activity
Dong Y., Nakagawa-Goto K., Lai C., Morris-Natschke S.L., Bastow K.F., Lee K.
Bioorganic and Medicinal Chemistry Letters, 2011
25.
Triacetic acid lactone production in industrial Saccharomyces yeast strains
Saunders L.P., Bowman M.J., Mertens J.A., Da Silva N.A., Hector R.E.
Journal of Industrial Microbiology and Biotechnology, 2015
27.
Screening for Enhanced Triacetic Acid Lactone Production by Recombinant Escherichia coli Expressing a Designed Triacetic Acid Lactone Reporter
Tang S., Qian S., Akinterinwa O., Frei C.S., Gredell J.A., Cirino P.C.
Journal of the American Chemical Society, 2013
28.
Microbial synthesis of triacetic acid lactone
Xie D., Shao Z., Achkar J., Zha W., Frost J.W., Zhao H.
Biotechnology and Bioengineering, 2006
29.
Engineering Escherichia coli to increase triacetic acid lactone (TAL) production using an optimized TAL sensor-reporter system
Li Y., Qian S., Dunn R., Cirino P.C.
Journal of Industrial Microbiology and Biotechnology, 2018
30.
Rewiring Yarrowia lipolytica toward triacetic acid lactone for materials generation
Markham K.A., Palmer C.M., Chwatko M., Wagner J.M., Murray C., Vazquez S., Swaminathan A., Chakravarty I., Lynd N.A., Alper H.S.
Proceedings of the National Academy of Sciences of the United States of America, 2018
31.
Bioengineering triacetic acid lactone production in Yarrowia lipolytica for pogostone synthesis
Yu J., Landberg J., Shavarebi F., Bilanchone V., Okerlund A., Wanninayake U., Zhao L., Kraus G., Sandmeyer S.
Biotechnology and Bioengineering, 2018
32.
Polyketide derivatives active against Botrytis cinerea in Gerbera hybrida
Koskela S., Söderholm P.P., Ainasoja M., Wennberg T., Klika K.D., Ovcharenko V.V., Kylänlahti I., Auerma T., Yli-Kauhaluoma J., Pihlaja K., Vuorela P.M., Teeri T.H.
Planta, 2010
33.
Bioinspired total synthesis of katsumadain A by organocatalytic enantioselective 1,4-conjugate addition
Wang Y., Bao R., Huang S., Tang Y.
Beilstein Journal of Organic Chemistry, 2013
35.
4-Hydroxy-6-alkyl-2-pyrones as nucleophilic coupling partners in Mitsunobu reactions and oxa-Michael additions
Burns M.J., Ronson T.O., Taylor R.J., Fairlamb I.J.
Beilstein Journal of Organic Chemistry, 2014
36.
10.1016/j.mencom.2019.01.001_sbref0065b
Zhang
Synthesis, 2007
38.
Synthesis and bioevaluation of a series of α-pyrone derivatives as potent activators of Nrf2/ARE pathway (part I)
Xi M., Sun Z., Sun H., Jia J., Jiang Z., Tao L., Ye M., Yang X., Wang Y., Xue X., Huang J., Gao Y., Guo X., Zhang S., Yang Y., et. al.
European Journal of Medicinal Chemistry, 2013
39.
Synthetic studies of fluorine-containing compounds for household insecticides
Mori T., Ujihara K., Matsumoto O., Yanagi K., Matsuo N.
Journal of Fluorine Chemistry, 2007
41.
2-Pyrones possessing antimicrobial and cytotoxic activities
Fairlamb I.J., Marrison L.R., Dickinson J.M., Lu F., Schmidt J.P.
Bioorganic and Medicinal Chemistry, 2004
45.
Bioactive 4-substituted-6-methyl-2-pyrones with promising cytotoxicity against A2780 and K562 cell lines
Marrison L.R., Dickinson J.M., Fairlamb I.J.
Bioorganic and Medicinal Chemistry Letters, 2002
50.
Pd-catalysed intramolecular regioselective arylation of 2-pyrones, pyridones, coumarins and quinolones by C–H bond functionalization
Nolan M., Bray J.T., Eccles K., Cheung M.S., Lin Z., Lawrence S.E., Whitwood A.C., Fairlamb I.J., McGlacken G.P.
Tetrahedron, 2014
51.
Pd/Pivalic Acid Mediated Direct Arylation of 2-Pyrones and Related Heterocycles
Pardo L.M., Prendergast A.M., Nolan M., Ó Muimhneacháin E., McGlacken G.P.
European Journal of Organic Chemistry, 2015
52.
Intramolecular Direct Arylation of 3-Halo-2-pyrones and 2-Coumarins
Nolan M., Pardo L.M., Prendergast A.M., McGlacken G.P.
Journal of Organic Chemistry, 2015
53.
Pd-catalysed regioselective C–H functionalisation of 2-pyrones
Burns M.J., Thatcher R.J., Taylor R.J., Fairlamb I.J.
Dalton Transactions, 2010
54.
Cyclization of 4-Phenoxy-2-coumarins and 2-Pyrones via a Double C–H Activation
Mackey K., Pardo L.M., Prendergast A.M., Nolan M., Bateman L.M., McGlacken G.P.
Organic Letters, 2016
55.
The reactivity of 4-hydroxy-6-methyl-2-pyrone towards aliphatic saturated and α,β-unsaturated aldehydes
de March P., Moreno-Mañas M., Casado J., Pleixats R., Roca J.L., Trius A.
Journal of Heterocyclic Chemistry, 1984
56.
A One-Pot Condensation of Pyrones and Enals. Synthesis of 1H,7H-5a,6,8,9-Tetrahydro-1-oxopyrano[4,3-b][1]benzopyrans
Hua D.H., Chen Y., Sin H., Maroto M.J., Robinson P.D., Newell S.W., Perchellet E.M., Ladesich J.B., Freeman J.A., Perchellet J., Chiang P.K.
Journal of Organic Chemistry, 1997
58.
A Formal [3 + 3] Cycloaddition Reaction. Improved Reactivity Using α,β-Unsaturated Iminium Salts and Evidence for Reversibility of 6π-Electron Electrocyclic Ring Closure of 1-Oxatrienes
Shen H.C., Wang J., Cole K.P., McLaughlin M.J., Morgan C.D., Douglas C.J., Hsung R.P., Coverdale H.A., Gerasyuto A.I., Hahn J.M., Liu J., Sklenicka H.M., Wei L., Zehnder L.R., Zificsak C.A., et. al.
Journal of Organic Chemistry, 2003
59.
Brønsted Acid‐Catalyzed Synthesis of Pyrans via a Formal [3+3] Cycloaddition
Hubert C., Moreau J., Batany J., Duboc A., Hurvois J., Renaud J.
Advanced Synthesis and Catalysis, 2008
60.
Metal-Free Brønsted Acid Catalyzed Formal [3 + 3] Annulation. Straightforward Synthesis of Dihydro-2H-Chromenones, Pyranones, and Tetrahydroquinolinones
Moreau J., Hubert C., Batany J., Toupet L., Roisnel T., Hurvois J., Renaud J.
Journal of Organic Chemistry, 2009
61.
A Lewis Acid-Catalyzed Formal [3 + 3] Cycloaddition of α,β-Unsaturated Aldehydes with 4-Hydroxy-2-Pyrone, Diketones, and Vinylogous Esters
Kurdyumov A.V., Lin N., Hsung R.P., Gullickson G.C., Cole K.P., Sydorenko N., Swidorski J.J.
Organic Letters, 2005
63.
Diastereoselective Synthesis of Polycyclic Acetal-Fused Pyrano[3,2-c]pyran-5(2H)-one Derivatives
Sagar R., Park J., Koh M., Park S.B.
Journal of Organic Chemistry, 2009
70.
Combined action of enzymes: the first domino reaction catalyzed by Agaricus bisporus
Leutbecher H., Hajdok S., Braunberger C., Neumann M., Mika S., Conrad J., Beifuss U.
Green Chemistry, 2009
79.
Catalytic Asymmetric Domino Michael Addition−Alkylation Reaction: Enantioselective Synthesis of Dihydrofurans
Rueping M., Parra A., Uria U., Besselièvre F., Merino E.
Organic Letters, 2010
81.
Triacetic acid lactone as a potential biorenewable platform chemical
Chia M., Schwartz T.J., Shanks B.H., Dumesic J.A.
Green Chemistry, 2012
82.
Engineering Catalyst Microenvironments for Metal-Catalyzed Hydrogenation of Biologically Derived Platform Chemicals
Schwartz T.J., Johnson R.L., Cardenas J., Okerlund A., Da Silva N.A., Schmidt-Rohr K., Dumesic J.A.
Angewandte Chemie - International Edition, 2014
86.
Iron-Catalyzed Cross-Coupling of Alkenyl Acetates
Gärtner D., Stein A.L., Grupe S., Arp J., Jacobi von Wangelin A.
Angewandte Chemie - International Edition, 2015
88.
Discovery of Multitarget Antivirals Acting on Both the Dengue Virus NS5-NS3 Interaction and the Host Src/Fyn Kinases
Vincetti P., Caporuscio F., Kaptein S., Gioiello A., Mancino V., Suzuki Y., Yamamoto N., Crespan E., Lossani A., Maga G., Rastelli G., Castagnolo D., Neyts J., Leyssen P., Costantino G., et. al.
Journal of Medicinal Chemistry, 2015
89.
10.1016/j.mencom.2019.01.001_sbref0245c
Castillo
Bull. Soc. Chim. Fr., 1982
91.
A combined ligand- and structure-based approach for the identification of rilmenidine-derived compounds which synergize the antitumor effects of doxorubicin
Vucicevic J., Srdic-Rajic T., Pieroni M., Laurila J.M., Perovic V., Tassini S., Azzali E., Costantino G., Glisic S., Agbaba D., Scheinin M., Nikolic K., Radi M., Veljkovic N.
Bioorganic and Medicinal Chemistry, 2016
93.
Design, synthesis and SAR of novel glucokinase activators.
Cheruvallath Z.S., Gwaltney S.L., Sabat M., Tang M., Feng J., Wang H., Miura J., Guntupalli P., Jennings A., Hosfield D., Lee B., Wu Y.
Bioorganic and Medicinal Chemistry Letters, 2013
94.
Bio-based triacetic acid lactone in the synthesis of azaheterocyclesviaa ring-opening transformation
Obydennov D.L., El-Tantawy A.I., Sosnovskikh V.Y.
New Journal of Chemistry, 2018
96.
Synthesis and characterization of some hydroxypyridone derivatives and their evaluation as antimicrobial agents
Faidallah H.M., Rostom S.A., Khan K.A., Basaif S.A.
Journal of Enzyme Inhibition and Medicinal Chemistry, 2012
97.
Reactions of Hydrazines with γ-Pyrones
Ainsworth C., Jones R.G.
Journal of the American Chemical Society, 1954
98.
B. Buettelmann, H. Knust, A. Thomas, US Patent, 20070082890, 2007.
99.
Synthesis of new heterocyclic compounds based on pyrazolopyridine scaffold and evaluation of their neuroprotective potential in MPP + -induced neurodegeneration
Jouha J., Loubidi M., Bouali J., Hamri S., Hafid A., Suzenet F., Guillaumet G., Dagcı T., Khouili M., Aydın F., Saso L., Armagan G.
European Journal of Medicinal Chemistry, 2017
100.
A one-pot process for the microwave-assisted synthesis of 7-substituted pyrazolo[1,5-a]pyrimidine
Bassoude I., Tber Z., Essassi E.M., Guillaumet G., Berteina-Raboin S.
RSC Advances, 2016
101.
One-step reaction leading to new pyrazolo[1,5-a]pyrimidines by condensation of 2-pyrone with 5(3)-amino-3(5)-arylpyrazoles
Bassoude I., Berteina-Raboin S., Leger J., Jarry C., Essassi E.M., Guillaumet G.
Tetrahedron, 2011
102.
Synthesis of new compounds containing the pyrazolo[3,4-b]pyridine-3-one subunit
Fadel S., Suzenet F., Hafid A., Rakib E.M., Khouili M., Pujol M.D., Guillaumet G.
Journal of Heterocyclic Chemistry, 2009
104.
A novel and direct synthetic route to substituted 1,5-dihydro-4H-[1]benzopyrano[4,3-b]pyridine-4,5-diones
Světlík J., Prónayová N., Hanuš V.
Journal of Heterocyclic Chemistry, 2000
105.
An Efficient Synthetic Access to Substituted Thiazolyl-pyrazolyl-chromene-2-ones from Dehydroacetic Acid and Coumarin Derivatives by a Multicomponent Approach
Ben Mohamed S., Rachedi Y., Hamdi M., Le Bideau F., Dejean C., Dumas F.
European Journal of Organic Chemistry, 2016
106.
A novel ratiometric fluorescent probe for selective detection of bisulfite in living cells
Chen Z., Chen F., Sun Y., Liu H., He H., Zhang X., Wang S.
RSC Advances, 2017
107.
Envirocat EPZ-10: An efficient catalyst for the synthesis of 3-acetoacetylcoumarins
Shaikh T.S., Undale K.A., Gaikwad D.S., Pore D.M.
Comptes Rendus Chimie, 2011
108.
Synthesis of novel 2H,8H-pyrano[2,3-f]chromene-2,8-diones from 8-formyl-7-hydroxy-4-methylcoumarin
Al-Kawkabani A., Boutemeur-Kheddis B., Makhloufi-Chebli M., Hamdi M., Talhi O., Silva A.M.
Tetrahedron Letters, 2013
110.
Novel benzopyranopyridine derivatives of 2-amino-3-formylchromone
Siddiqui Z., Praveen S., Farooq F.
Chemical Papers, 2010
113.
Synthesis of C3-dihydrofuran substituted coumarins via multicomponent approach
Tangeti V.S., Varma K. R., Siva Prasad G.V., Satyanarayana K.V.
Synthetic Communications, 2016
117.
Synthesis of new series of 1-Aryl-1,4-dihydro-4-oxo-6-methyl pyridazine-3-carboxylic acid as potential antibacterial agents
Nagawade R.R., Khanna V.V., Bhagwat S.S., Shinde D.B.
European Journal of Medicinal Chemistry, 2005
119.
Synthesis andin-vitroCytotoxic Evaluation of Novel Pyridazin-4-one Derivatives
Mojahidi S., Rakib E.M., Sekkak H., Abouricha S., Benchat N., Mousse H.A., Zyad A.
Archiv der Pharmazie, 2010
120.
Synthesis of New Azocompounds and Fused Pyrazolo[5,1-c][1,2,4]triazines Using Heterocyclic Components
Ledenyova I.V., Didenko V.V., Shestakov A.S., Shikhaliev K.S.
Journal of Heterocyclic Chemistry, 2013
121.
Pyrazolopyridinones as functionally selective GABAA ligands
Blackaby W.P., Atack J.R., Bromidge F., Lewis R., Russell M.G., Smith A., Wafford K., McKernan R.M., Street L.J., Castro J.L.
Bioorganic and Medicinal Chemistry Letters, 2005
122.
[4-(Phenoxy)pyridin-3-yl]methylamines: A new class of selective noradrenaline reuptake inhibitors
Fish P.V., Ryckmans T., Stobie A., Wakenhut F.
Bioorganic and Medicinal Chemistry Letters, 2008
123.
4-Oxo-1,4-dihydropyridines as Selective CB2 Cannabinoid Receptor Ligands: Structural Insights into the Design of a Novel Inverse Agonist Series
El Bakali J., Muccioli G.G., Renault N., Pradal D., Body-Malapel M., Djouina M., Hamtiaux L., Andrzejak V., Desreumaux P., Chavatte P., Lambert D.M., Millet R.
Journal of Medicinal Chemistry, 2010
124.
SYNTHESIS OF 3-ACETOACETYL-7-METHYL-2H,5H-PYRANO[4,3-B]PYRAN-2,5-DIONE
Boutemeur-Kheddis B., Bendaas A., Hamdi M., Sakellariou R., Spéziale V.
Organic Preparations and Procedures International, 1994
125.
Study of the reactions of 3-acetoacetyl-7-methyl-2H,5H-pyrano[4,3-b]pyran-2,5-dione with aromatic amines
Boutemeur-Kheddis B., Hamdi M., Sellier N., Silva A.M.
Journal of Heterocyclic Chemistry, 2001
126.
Polyunsaturated C-Glycosidic 4-Hydroxy-2-pyrone Derivatives: Total Synthesis Shows that Putative Orevactaene Is Likely Identical with Epipyrone A
Preindl J., Schulthoff S., Wirtz C., Lingnau J., Fürstner A.
Angewandte Chemie - International Edition, 2017
127.
Total Synthesis and Stereochemical Assignment of (±)-Sorbiterrin A
Qi C., Qin T., Suzuki D., Porco J.A.
Journal of the American Chemical Society, 2014
128.
α-pyrones : Small molecules with versatile structural diversity reflected in multiple pharmacological activities-an update
Bhat Z.S., Rather M.A., Maqbool M., Lah H.U., Yousuf S.K., Ahmad Z.
Biomedicine and Pharmacotherapy, 2017