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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 19
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Original Articles

New Syntheses of Geiparvarin and 2,5-Dimethyl-3(2H)-furanone Via Co2 Mediated Bond Reorganization

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Pages 3063-3068 | Received 13 Aug 1990, Published online: 24 Oct 2006

References

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  • Inoue , Y. , Ohuchi , K. and Imaizumi , S. 1988 . Tetrahedron Lett. , 29 : 5941 Inoue, Y., Ohuchi, K., Yen, I.-F., and Imaizumi, S., Bull. Chem. Soc. Jpn., 1989, 62, 3518.
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  • Christy , M. E. , Anderson , P. S. , Britcher , S. F. , Colton , C. D. , Evans , B. E. , Remy , D. C. and Engelhardt , E. L. 1979 . J. Org. Chem. , 44 : 3117
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  • All new compounds gave satisfactory C and H combustion analysis and/or appropriate parent ion identification by high resolution mass spectrometry. Selected spectral data are given. 6 mp 92.0–93.0°C; IR (KBr) 3450, 1690, 1610 cm−1; 1H NMR (CDCl3) δ 1.75 (s, 3H), 2.47 (s, 1H), 4.07 (s, 2H), 4.60 (d, 2H), 5.72 (t, 1H), 6.25 (d, 1H), 6.75 (t, 1H), 6.83 (dd, 1H), 7.35 (dd, 1H), 7.62 (d, 1H). 7 mp 170.9–173.3°C (dec.); IR (KBr) 1720, 1690, 1610 cm−1; 1H NMR (CDCl3) δ 1.87 (s, 3H), 14.92 (d, 2H), 6.26 (d, 1H), 6.64 .(t, 1H), 6.75 (t, 1H), 6.83 (dd, 1H), 7.35 (dd, 1H), 7.62 (d, 1H), 9.43 (s, 1H). 8 IR (film) 3400, 1720, 1620 cm−1; 1H NMR (CDCl3) δ 1.52 (s, 6H), 1.86 (s, 3H), 3.24 (s, 1H), 3.42 (s, 1H), 4.60 (d, 2H), 4.82 (s, 1H), 5.88 (t, 1H), 6.25 (d, 1H), 6.64 (t, 1H), 6.75 (t, 1H), 6.83 (dd, 1H), 7.35 (dd, 1H), 7.62 (d, IH). 9 mp 132.6–133.8°C; IR (KBr) 3400, 1720, 1620J cm−1; 1H NMR (CDCl3) δ1.60 (s, 6H), 1.90 (s, 3H), 2.74 (s, 1H), 4.84 (d, 2H), 6.25 (d, 1H), 6.75 (t, 1H), 6.83 (dd, 1H), 7.18 (t, 1H), 7.35 (dd, 1H), 7.62 (d, 1H).
  • Venturello , C. and D'Aloisio , R. 1977 . Synthesis , : 754 Andersen, S.H., Das, N.B., J⊘rgensen, R.D., Kjeldsen, G., Knudsen, J.S., Sharma, S.C., and Torssell, K.B.G., Acta Chem. Scand., 1982, 1.
  • Goldschmidt , S. and Zoebelein , A. 1961 . Chem. Ber. , 94 : 169
  • Arcadi , A. , Cacchi , S. , Marinelli , F. and Misiti , D. 1988 . Tetrahedron Lett. , 29 : 1457
  • The purity was 90%, 3-hexen-2,5-dione being the byproduct.

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