Synthesis of Fatty 1,2,4-Trioxanes by Peracetalization of β-Hydroxy Hydroperoxides

Thomas De Dios Miguel; Dan Louvel; Killian Onida; Adeline Lavoignat; Stephane Picot; Nicolas Duguet

doi:10.1055/a-1643-3057

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(03): 617-628
DOI: 10.1055/a-1643-3057

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Synthesis of Fatty 1,2,4-Trioxanes by Peracetalization of β-Hydroxy Hydroperoxides

Thomas De Dios Miguel

^aUniv Lyon, Université Claude Bernard Lyon1, CNRS, INSA, CPE-Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, ICBMS, UMR 5246, Equipe CAtalyse, SYnthèse et ENvironnement (CASYEN), Bâtiment Lederer, 1 rue Victor Grignard, F-69100 Villeurbanne, France

,

Dan Louvel

^aUniv Lyon, Université Claude Bernard Lyon1, CNRS, INSA, CPE-Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, ICBMS, UMR 5246, Equipe CAtalyse, SYnthèse et ENvironnement (CASYEN), Bâtiment Lederer, 1 rue Victor Grignard, F-69100 Villeurbanne, France

,

Killian Onida

^aUniv Lyon, Université Claude Bernard Lyon1, CNRS, INSA, CPE-Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, ICBMS, UMR 5246, Equipe CAtalyse, SYnthèse et ENvironnement (CASYEN), Bâtiment Lederer, 1 rue Victor Grignard, F-69100 Villeurbanne, France

,

Adeline Lavoignat

^bUniv Lyon, Université Claude Bernard Lyon1, CNRS, INSA, CPE-Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, ICBMS, UMR 5246, Equipe Synthèse de Molécules d’Intérêt Thérapeutique (SMITH), Bâtiment Raulin, 43 boulevard du 11 novembre 1918, F-69622 Villeurbanne cedex, France

,

Stephane Picot

^bUniv Lyon, Université Claude Bernard Lyon1, CNRS, INSA, CPE-Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, ICBMS, UMR 5246, Equipe Synthèse de Molécules d’Intérêt Thérapeutique (SMITH), Bâtiment Raulin, 43 boulevard du 11 novembre 1918, F-69622 Villeurbanne cedex, France

^cParasitology and Mycology Department, Institute of Infectious Agents, Hôpital de la Croix-Rousse, Hospices Civils de Lyon, Lyon F-69004, France

,

Nicolas Duguet ∗

^aUniv Lyon, Université Claude Bernard Lyon1, CNRS, INSA, CPE-Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, ICBMS, UMR 5246, Equipe CAtalyse, SYnthèse et ENvironnement (CASYEN), Bâtiment Lederer, 1 rue Victor Grignard, F-69100 Villeurbanne, France

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Abstract

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Abstract

The peracetalization of a β-hydroxy hydroperoxide derived from methyl oleate was studied using benzaldehyde as a model substrate to give the corresponding fatty 1,2,4-trioxane. The desired product was obtained as a mixture of regioisomers but only one diastereoisomer of each was formed. The nature of the acid catalyst was studied and both p-toluene sulfonic acid (PTSA) and Amberlyst A35 (A35) were found to be efficient homogeneous and heterogeneous catalysts, respectively. The nature of the solvent was also investigated and ethereal solvents such as 2-methyltetrahydrofuran (2-MeTHF), methyl tert-butyl ether (MTBE) and cyclopentyl methyl ether (CPME) gave the best NMR yield (85%) for the preparation of the fatty trioxane. The optimized conditions were applied to a range of aromatic and aliphatic aldehydes, and the corresponding 1,2,4-trioxanes were isolated with 30–91% yields (21 examples). The antimalarial activity of three trioxanes was studied against Plasmodium falciparum, however, no significant activity was detected (IC₅₀ >1600 nM).

Key words

β-hydroxy hydroperoxides - aldehydes - peracetalization - 1,2,4-trioxanes - fatty acids

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References

1a Saito I, Nittala SS. Endoperoxides . In Peroxides . J. Wiley & Sons; Chichester: 1983: 311-374
1b Bouillon G, Lick C, Schank K. Diacyl Peroxides, Peroxycarboxylic Acids and Peroxy Esters . In Peroxides . J. Wiley & Sons; Chichester: 1983: 279-309
1c Ando W. Organic Peroxides . Wiley; Chichester: 1992
1d Yaremenko IA, Vil VA, Demchuk DV, Terent’ev AO. Beilstein J. Org. Chem. 2016; 12: 1647
1e Žmitek K, Zupan M, Iskra J. Org. Biomol. Chem. 2007; 5: 3895
1f Gandhi H, O’Reilly K, Gupta MK, Horgan C, O’Leary EM, O’Sullivan TP. RSC Adv. 2017; 7: 19506
1g Terent’ev AO, Borisov DA, Vil’ VA, Dembitsky VM. Beilstein J. Org. Chem. 2014; 10: 34

2a Galal AM, Ross SA, Jacob M, ElSohly MA. J. Nat. Prod. 2005; 68: 1274
2b Buragohain P, Surineni N, Barua NC, Bhuyan PD, Boruah P, Borah JC, Laisharm S, Moirangthem DS. Bioorg. Med. Chem. Lett. 2015; 25: 3338

3a Liu G, Song S, Liu X, Zhang A, Miao Z, Ding C. RSC Adv. 2016; 6: 98975
3b Zhang B. Arch. Pharm. 2020; 353: 1900240
3c Kotammagari TK, Paul S, Barik GK, Santra MK, Bhattacharya AK. Org. Biomol. Chem. 2020; 18: 2252

4 Chaudhary S, Sharma V, Jaiswal PK, Gaikwad AN, Sinha SK, Puri SK, Sharon A, Maulik PR, Chaturvedi V. Org. Lett. 2015; 17: 4948

5a Eckstein-Ludwig U, Webb RJ, van Goethem ID. A, East JM, Lee AG, Kimura M, O’Neill PM, Bray PG, Ward SA, Krishna S. Nature 2003; 424: 957
5b Krishna S, Uhlemann AC, Haynes RK. Drug Resist. Updates 2004; 7: 233
5c Haynes RK, Chan WC, Lung C.-M, Uhlemann A.-C, Eckstein U, Taramelli D, Parapini S, Monti D, Krishna S. ChemMedChem 2007; 2: 1480

6a Kepler JA, Philip A, Lee YW, Morey MC, Carroll FI. J. Med. Chem. 1988; 31: 713
6b Tang Y, Dong Y, Vennerstrom JL. Med. Res. Rev. 2004; 24: 425
6c Yang P, Lu M, Li K, Xie Y. J. Heterocycl. Chem. 2020; 57: 526
6d Meshnick SR, Taylor TE, Kamchonwongpaisan S. Microbiol. Rev. 1996; 60: 301
6e Vroman JA, Alvim-Gaston M, Avery MA. Curr. Pharm. Des. 1999; 5: 101

7a Jefford CW, Jin S.-J, Bernardinelli G. Tetrahedron Lett. 1991; 32: 7243
7b Jefford CW, Jin S.-J, Bernardinelli G. Helv. Chim. Acta 1997; 80: 2440

8 Mischne MP, Huber SN, Zinczuk J. Can. J. Chem. 1999; 77: 237
9 Jefford CW, Velarde JA, Bernardinelli G, Bray DH, Warhurst DC, Milhous WK. Helv. Chim. Acta 1993; 76: 2775
10 Jefford CW, Deheza MF, Wang JB. Heterocycles 1997; 46: 451

11a Louvel D, De Dios Miguel T, Vu ND, Duguet N. Eur. J. Org. Chem. 2021; 2990
11b Bordier C, Escande V, Darcel C. Tetrahedron 2021; 97: 132379

For selected works on the formation of β-hydroxy hydroperoxides by ene-reaction of allylic alcohols with singlet oxygen, see:

12a Singh C. Tetrahedron Lett. 1990; 47: 6901
12b Adam W, Nestler B. J. Am. Chem. Soc. 1992; 114: 6549
12c Adam W, Nestler B. J. Am. Chem. Soc. 1993; 115: 5041
12d Adam W, Nestler B. Tetrahedron Lett. 1993; 34: 611
12e Singh C, Malik H. Org. Lett. 2005; 7: 5673
12f Griesbeck AG, El-Idreesy TT, Lex J. Tetrahedron 2006; 62: 10615
12g Clennan EL, Zhang D, Singleton J. Photochem. Photobiol. 2006; 82: 1226
12h Hall JF. B, Bourne RA, Han X, Earley JH, Poliakoff M, George MW. Green Chem. 2013; 15: 177

For selected works on the formation of β-hydroxy hydroperoxides by ring-opening of epoxides with H₂O₂, see:

13a Adam W, Peters K, Renz M. J. Org. Chem. 1997; 62: 3183
13b Subramanyam V, Brizuela CL, Soloway AH. J. Chem. Soc., Chem. Commun. 1976; 508
13c Ogata Y, Sawaki Y, Shimizu H. J. Org. Chem. 1978; 43: 1760
13d Yan X, Qiao C, Guo Z. Synlett 2013; 24: 502
13e Liu Y.-H, Zhang Z.-H, Li T.-S. Synthesis 2008; 3314
13f Li Y, Hao H.-D, Wu Y. Org. Lett. 2009; 11: 2691
13g Li PH, Li BL, An ZM, Mo LP, Cui ZS, Zhang ZH. Adv. Synth. Catal. 2013; 355: 2952
13h Liu Y.-H, Hu H.-C, Ma Z.-C, Dong Y.-F, Wang C, Pang Y.-M. Monatsh. Chem. 2017; 149: 551

14 Payne GB, Smith CW. J. Org. Chem. 1957; 22: 1682

15a Tang Y, Dong Y, Wang X, Sriraghavan K, Wood JK, Vennerstrom JL. J. Org. Chem. 2005; 70: 5103
15b Sabbani S, Stocks PA, Ellis GL, Davies J, Hedenstrom E, Ward SA, O’Neill PM. Bioorg. Med. Chem. Lett. 2008; 18: 5804
15c Sabbani S, La Pensée L, Bacsa J, Hedenström E, O’Neill PM. Tetrahedron 2009; 65: 8531

16 Hao H.-D, Li Y, Han W.-B, Wu Y. Org. Lett. 2011; 13: 4212

17a Griesbeck AG, El-Idreesy TT, Fiege M, Brun R. Org. Lett. 2002; 4: 4193
17b Griesbeck AG, El-Idreesy TT, Hoinck LO, Lex J, Brun R. Bioorg. Med. Chem. Lett. 2005; 15: 595
17c Griesbeck AG, Schlundt V, Neudörfl JM. RSC Adv. 2013; 3: 7265
17d Griesbeck AG, Höinck L.-O, Neudörfl JM. Beilstein J. Org. Chem. 2010; 6 61; DOI: 10.3762/bjoc.6.61

18 Zhang M, Han Y, Niu J.-L, Zhang Z.-H. Adv. Synth. Catal. 2017; 359: 3618
19 Adam W, Rios A. J. Chem. Soc. D, Chem. Commun. 1971; 822
20 Griesbeck AG, Blunk D, El-Idreesy TT, Raabe A. Angew. Chem. Int. Ed. 2007; 46: 8883 ; Angew. Chem. 2007, 119, 9040
21 Amado PS. M, Frija LM. T, Coelho JA. S, O’Neill PM, Cristiano ML. S. J. Org. Chem. 2021; 86: 10608

22a Vu ND, Guicheret B, Duguet N, Metay E, Lemaire M. Green Chem. 2017; 19: 3390
22b Guicheret B, Bertholo Y, Blach P, Raoul Y, Metay E, Lemaire M. ChemSusChem 2018; 11: 3431
22c Guicheret B, Da Silva E, Philippe R, Favre-Reguillon A, Vanoye L, Blach P, Raoul Y, De Bellefon C, Metay E, Lemaire M. ACS Sustainable Chem. Eng. 2020; 8: 13167
22d Bouchakour M, Daaou M, Duguet N. Eur. J. Org. Chem. 2021; 1647

23a Deruer E, Duguet N, Lemaire M. ChemSusChem 2015; 8: 2481
23b Vu ND, Bah S, Deruer E, Duguet N, Lemaire M. Chem. Eur. J. 2018; 24: 8141
23c Charvieux A, Vu ND, Duguet N, Lemaire M. Eur. J. Org. Chem. 2019; 1251
23d Vu ND, Chavallard R, De Dios Miguel T, Duguet N, Lemaire M. ACS Sustainable Chem. Eng. 2019; 7: 13865
23e Akhdar A, Onida K, Vu ND, Grollier K, Norsic S, Boisson C, D’Agosto F, Duguet N. Adv. Sustainable Syst. 2021; 5: 2000218

24 De Dios Miguel T, Vu ND, Lemaire M, Duguet N. ChemSusChem 2021; 14: 379

25a Sutter M, Pehlivan L, Lafon R, Dayoub W, Raoul Y, Métay E, Lemaire M. Green Chem. 2013; 15: 3020
25b Sutter M, Dayoub W, Métay E, Raoul Y, Lemaire M. ChemCatChem 2013; 5: 2893

26 Bacon DJ, Latour C, Lucas C, Colina O, Ringwald P, Picot S. Antimicrob. Agents Chemother. 2007; 51: 1172

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