Preparation of Bicyclic 1,2,4-trioxanes from Gamma,delta-unsaturated Ketones

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2009 Jan 10

PMID 19132925

Citations 3

Authors

Armando P Ramirez

Andrew M Thomas

K A Woerpel

Affiliations

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Abstract

Treatment of gamma,delta-unsaturated ketones with hydrogen peroxide and acid provides a rapid entry into the medicinally important 1,2,4-trioxane structure. Alkene substitution that stabilizes carbocationic intermediates proved to be important for the success of this transformation.

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References

Jefford C . Synthetic peroxides as antimalarials. Curr Opin Investig Drugs. 2004; 5(8):866-72. View

Romero M, Efferth T, Serrano M, Castano B, Macias R, Briz O . Effect of artemisinin/artesunate as inhibitors of hepatitis B virus production in an "in vitro" replicative system. Antiviral Res. 2005; 68(2):75-83. DOI: 10.1016/j.antiviral.2005.07.005. View

Wu Y . How might qinghaosu (artemisinin) and related compounds kill the intraerythrocytic malaria parasite? A chemist's view. Acc Chem Res. 2002; 35(5):255-9. DOI: 10.1021/ar000080b. View

Ceruti M, Balliano G, Viola F, Grosa G, Rocco F, Cattel L . 2,3-Epoxy-10-aza-10,11-dihydrosqualene, a high-energy intermediate analogue inhibitor of 2,3-oxidosqualene cyclase. J Med Chem. 1992; 35(16):3050-8. DOI: 10.1021/jm00094a020. View

Sachs J, Malaney P . The economic and social burden of malaria. Nature. 2002; 415(6872):680-5. DOI: 10.1038/415680a. View

Barnes K, White N . Population biology and antimalarial resistance: The transmission of antimalarial drug resistance in Plasmodium falciparum. Acta Trop. 2005; 94(3):230-40. DOI: 10.1016/j.actatropica.2005.04.014. View

Hien T, White N . Qinghaosu. Lancet. 1993; 341(8845):603-8. DOI: 10.1016/0140-6736(93)90362-k. View

Jefford C . Why artemisinin and certain synthetic peroxides are potent antimalarials. Implications for the mode of action. Curr Med Chem. 2002; 8(15):1803-26. DOI: 10.2174/0929867013371608. View

Klayman D . Qinghaosu (artemisinin): an antimalarial drug from China. Science. 1985; 228(4703):1049-55. DOI: 10.1126/science.3887571. View

10.

Zmitek K, Zupan M, Iskra J . Alpha-substituted organic peroxides: synthetic strategies for a biologically important class of gem-dihydroperoxide and perketal derivatives. Org Biomol Chem. 2007; 5(24):3895-908. DOI: 10.1039/b711647k. View

11.

Jansen F, Soomro S . Chemical instability determines the biological action of the artemisinins. Curr Med Chem. 2008; 14(30):3243-59. DOI: 10.2174/092986707782793844. View

12.

Ramirez A, Woerpel K . Synthesis of 1,2-dioxolanes by annulation reactions of peroxycarbenium ions with alkenes. Org Lett. 2005; 7(21):4617-20. DOI: 10.1021/ol051703u. View

13.

Stoll M, Hinder M, Ruzicka L . Steroids and sex hormones; Cycloheptadecane-dione-1,9. Helv Chim Acta. 1948; 31(4):1176-8. DOI: 10.1002/hlca.19480310426. View

14.

Mayr H, Kempf B, Ofial A . Pi-nucleophilicity in carbon-carbon bond-forming reactions. Acc Chem Res. 2003; 36(1):66-77. DOI: 10.1021/ar020094c. View

15.

Woodrow C, Krishna S . Antimalarial drugs: recent advances in molecular determinants of resistance and their clinical significance. Cell Mol Life Sci. 2006; 63(14):1586-96. PMC: 11136207. DOI: 10.1007/s00018-006-6071-1. View

16.

Dembitsky V . Bioactive peroxides as potential therapeutic agents. Eur J Med Chem. 2007; 43(2):223-51. DOI: 10.1016/j.ejmech.2007.04.019. View

17.

Woodrow C, Haynes R, Krishna S . Artemisinins. Postgrad Med J. 2005; 81(952):71-8. PMC: 1743191. DOI: 10.1136/pgmj.2004.028399. View

18.

Jin H, Liu H, Zhang Q, Wu Y . On the susceptibility of organic peroxy bonds to hydride reduction. J Org Chem. 2005; 70(11):4240-7. DOI: 10.1021/jo050139y. View

19.

Dhingra V, Vishweshwar Rao K, Narasu M . Current status of artemisinin and its derivatives as antimalarial drugs. Life Sci. 2000; 66(4):279-300. DOI: 10.1016/s0024-3205(99)00356-2. View

20.

Efferth T . Mechanistic perspectives for 1,2,4-trioxanes in anti-cancer therapy. Drug Resist Updat. 2005; 8(1-2):85-97. DOI: 10.1016/j.drup.2005.04.003. View