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Absolute structure of (11E, 1S, 3S, 4R, 7S, 8R, 14S)-3,7-diiodo-4,8-epoxy-euniolide

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Abstract

3,7-Diiodo-4,8-epoxy-euniolide (2) was synthesized from euniolide (1) by the addition reaction of iodine in the presence of triphenylphosphine in CH2Cl2. The absolute structure of 2 was unambiguously determined by a combination of 1H and 13C NMR, HREI mass spectroscopy, and x-ray single crystal analysis as (11E, 1S, 3S, 4R, 7S, 8R, 14S)-3,7-diiodo-4,8-epoxy-cembra-11,15-dien-16,14-olide. X-ray crystallographic data for 2: Orthorhombic P212121 (#19), a = 10.9688(7), b = 11.3909(8), c = 16.885(1) Å, ρcalcd = 1.795 g cm−3, and for Z = 4.

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References

  1. Faulkner, D.J. Nat. Prod. Rep. 1996, 13, 75.

    Google Scholar 

  2. Morales, J.J.; Espina, J.R.; Rodríguez, A.D. Tetrahedron 1990, 46, 5889.

    Google Scholar 

  3. Eterovic, V.A.; Hann, R.M.; Ferchmin, P.A.; Rodríguez, A.D.; Li, L.; Lee, Y.H.; McNamee, M.G. Cell. Mol. Neurobiol. 1993, 13, 99.

    Google Scholar 

  4. Eterovic, V.A.; Li, L.; Ferchmin, P.A.; Lee, Y.H.; Hann, R.M.; Rodríguez, A.D.; McNamee, M.G. Cell. Mol. Neurobiol. 1993, 13, 111.

    Google Scholar 

  5. Rodríguez, A.D.; Piña, I.C.; Barnes, C.L. J. Org. Chem. 1995, 60, 8096.

    Google Scholar 

  6. Siemens Analytical X-ray Systems, Inc. SAINT program version 4. 1994–1996, 6300 Enterprise Lane, Madison, WI 53719.

  7. Molecular structure corporation. teXsan single crystal structure analysis software. version 1.7. MSC, 1992–1997, 3200 Research Forest Drive, The Woodlands, TX 77381.

    Google Scholar 

  8. Marshall, J.A.; Karas, L.J.; Coghlan, M.J. J. Org. Chem. 1982, 47, 699.

    Google Scholar 

  9. Marshall, J.A.; Andrews, R.C.; Lebioda, L. J. Org. Chem. 1987, 52, 2378.

    Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, University of Puerto Rico, San Juan, Puerto Rico, 00931

    Abimael D. Rodríguez, Ana L. Acosta & Songping D. Huang

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  1. Abimael D. Rodríguez
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  2. Ana L. Acosta
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  3. Songping D. Huang
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Rodríguez, A.D., Acosta, A.L. & Huang, S.D. Absolute structure of (11E, 1S, 3S, 4R, 7S, 8R, 14S)-3,7-diiodo-4,8-epoxy-euniolide. Journal of Chemical Crystallography 28, 17–21 (1998). https://doi.org/10.1023/A:1021718416971

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  • DOI: https://doi.org/10.1023/A:1021718416971

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