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The pseudoguaianolide isoconfertiflorin

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Abstract

The sesquiterpene lactone isoconfertiflorin, C17H22O5, 1, crystallizes in trigonal space group P31 with a = 10.4498(5), c = 12.7516(8) Å, V = 1205.9(2) Å3, and Z = 3. It differs from confertiflorin in having an endocyclic C=C bond in the lactone ring, which carries an exocyclic methyl group. The seven-membered ring adopts an approximate twist-chair conformation with C10 lying in the local two-fold axis, and asymmetry parameter ΔC2 = 5.8°. The cyclopentanone ring has the half-chair conformation with C4 on the local two-fold axis, and ΔC2 = 0.9°. The lactone ring is almost planar with maximum deviation 0.014(2) Å. Both methyl groups on the 7-membered ring are β–oriented. The acetyl group at C8 has an α orientation.

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Authors and Affiliations

  1. Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana, 70803

    José Castañeda-Acosta, Howard G. Pentes, Frank R. Fronczek & Nikolaus H. Fischer

Authors
  1. José Castañeda-Acosta
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  2. Howard G. Pentes
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  3. Frank R. Fronczek
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  4. Nikolaus H. Fischer
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Correspondence to Frank R. Fronczek.

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Castañeda-Acosta, J., Pentes, H.G., Fronczek, F.R. et al. The pseudoguaianolide isoconfertiflorin. Journal of Chemical Crystallography 29, 1057–1059 (1999). https://doi.org/10.1023/A:1009537203839

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