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Natural Product Letters Volume 7, 1995 - Issue 1
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Original Articles

A Simple and Efficient Approach for the Synthesis of a 1,2,4-Trioxane related to Artemisinin

Silvia N. Huber Instituto de Química Orgánica de Síntesis (CONICET-UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Casilla de Correo 991, 2000, Rosario, Argentina
&
Mirta P. Mischne Instituto de Química Orgánica de Síntesis (CONICET-UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Casilla de Correo 991, 2000, Rosario, Argentina
Pages 43-46 | Received 12 May 1995, Published online: 04 Oct 2006

References

  • Butler , A. R. and Wu , Y-L. 1992 . Artemisinin (Qinghaosu): A New Type of Antimalarial Drug . Chemical Society Rewiews , 85 : 85 – 90 .
  • Jung , M. 1994 . Current Developments in the Chemistry of Artemisinin and Related Compounds . Current Medicinal Chemistry , 1 : 35 – 49 . and references cited therein
  • Adam , W. , Klein , V. , Mosandl , T. , Peters , G. , Peters , K. and von Schenering , H. G. 1988 . Preparative Visible-Laser Photochemistry: Qinghaosu-Type 1,2,4-Trioxanes by Molecular Oxygen Trapping of Paterno-Buchi Triplet 1,4-Diradicals Derived from 3,4-Dihydro-4,4-dimethyl-2H-pyran-2-one and Quinones . Journal of Organic Chemistry , 53 : 4986 – 4992 .
  • Jefford , C. , Jin , S. J. and Bernardinelli , G. 1991 . Reactions of an Endoperoxide with Chiral Ketones. Diasteroselective Formation of 1,2,4-Trioxanes and 1,3-Dioxolanes . Tetrahedron Letters , 32 : 7243 – 7246 .
  • Bloodworth , A. J. and Johnson , K. A. 1994 . 6-Hydroxymethyl-1,2,4-Trioxanes and Derivatives: An Alternative 1,2,4-Trioxane Synthesis from β'γ-Unsaturated β-Hydroxyhydroperoxides . Tetrahedron Letters , 35 : 8057 – 8060 .
  • These irradiations were performed in a Rayonet RPR 100 photochemical reactor equipped with 16 lamps, λ 350nm, in which centre a transparent pyrex vessel was placed. This vessel contained a solution of β-ionone (2a) (75mg, 0.39 mmol) in benzene or toluene (20 ml). A stream of oxygen was passed through the solution. After 6 h. the solvent was evaporated under reduced pressure and the residue thus obtained was purified by column chromatography (SiO2 increasing amounts of EtOAc in hexane as solvent) vielding 3a (41 mg, 47%)
  • Properties of 3a: IR: 2935, 1384, 1108, 985 cm−1; 1H NMR (200 MHz, CDCl3) δ= 1.01 (3H, s), 1.11 (3H, s), 1.14 (3H, s), 1.47 (3H, s), 6.42 (1H, d, J= 8.5 Hz), 6.53 (1H, d, J= 8.5 Hz). 13C NMR (50 MHz, CDCl3) δ= 19.17 (t), 20.74 (q), 24.30 (q), 25.33 (q), 26.49 (q), 34.46 (t), 34.46 (t), 35.47 (s), 77.98 (s), 82.01 (s), 94.51 (s), 128.41 (d), 133.24 (d). The 1H NMR data for compound 3a are in agreement with those reported in ref. 8
  • Etoh , H. , Ina , K. and Iguchi , M. 1973 . Photosensitised Oxygenation of α-Pyran Derived from β-Ionone . Agricultural and Biological Chemistry , 37 : 2241 – 2244 .
  • Mathies , P. , Nishio , T. , Frei , B. and Jeger , O . 1989 . 102- Photochemical Reactions . Helvetica Chimica Acta , 72 : 933 – 942 .
  • Nishio , T. , Mathies , P. , Job , K. , Frei , B. and Jeger , O. 1989 . 103-Photochemical Reactions . Helvetica Chimica Acta , 72 : 943 – 951 .
  • Cerfontain , H. and Geenevasen , J. A.J. 1981 . Photochemistry of Dienones-VIII . Tetrahedron , 37 : 1571 – 1573 .
  • Mousseron-Canet , M. , Mani , J-C. and Dalle , J-P. 1967 . Photooxydation sensibiliseé dans la série de la β-Ionone . Bulletin de la Société Chimique de France , : 608 – 612 .
  • Properties of 3c: colorless crystals from isopropyl ether, m.p. 51–52.5°C. IR (KBr): 2937, 2351, 1742, 1376, 1061 cm−1, 1H NMR (200 MHz, CDCl3) δ= 1.00 (3H, s), 1.10 (3H, s), 1.14 (3H, s), 2.78 (2H, s), 3.70 (3H, s), 6.54 (1H, d, J= 8.6 Hz), 6.77 (1H, d, J= 8.5 Hz), 13C NMR (50 MHz, CDCl3) δ= 19.09 (t), 24.31 (q), 25.37 (q), 26.44 (q), 34.38 (t), 34.45 (t), 39.18 (t), 35.58 (s), 51.88 (q), 77.53 (s), 82.57 (s), 94.34 (s), 128.01(d), 131.97 (d), 168.09 (s). MS m/z: 250 (M+ −32), 109(32), 69(49), 43(54). (Found: C, 63.64; H, 7.72. C15H22O5: C, 63.81; H, 7.85%)
  • Properties of 8: colorless oil IR: 3433, 2937, 1463, 1098 cm−1. 1H NMR (200 MHz, CDCl3) δ= 1.01 (3H, s), 1.06 (3H, s), 1.30 (3H, s), 1.36 (3H, s), 2.99 (1H, s), 2.12(1H, d), 5.46 (1H, dd, J= 4Hz and J= 10Hz). 13C NMR (50 MHz, CDCl3) δ= 19.47 (t), 22.66 (q), 24.01 (q), 29.02 (q), 32.14 (q), 36.20 (t), 36.58 (s), 36.59 (t), 40.19 (t), 88.19 (s), 106.14 (s), 114.9 (d), 150.83 (s). MS m/z: 193 (M+-32–1), 135 (28.86), 109 (19.75), 93 (39.25), 55 (29.32), 43(100)
  • Properties of 9: colorless oil IR: 3213, 2935, 1459, 1132 cm1. 1H NMR (200 MHz, CDCl3) δ= 0.81 (3H, s), 0.95 (3H, s), 1.24(3H, s), 4.74 (1H, s), 5.04 (1H, s). 13C NMR (50 MHz, CDCl3) δ= 19.0 (t), 22.95 (q), 23.75 (q), 25.21 (q), 24.09 (t), 29.96 (t), 32.56 (t), 36.20 (t), 39.60 (s), 85.27 (s), 96.78 (s), 111.57 (t), 146.97 (s)

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