Conformations of bryonolic acid and its derivatives in CDCl<sub>3</sub> solution by <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy

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公開日
1987-10
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/mrc.1260251004
公開者
Wiley

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<jats:title>Abstract</jats:title><jats:p>Comparison of the <jats:sup>1</jats:sup>H and <jats:sup>13</jats:sup>C chemical shift data of bryonolic acid (D : C‐friedoolean‐8‐en‐3β‐ol‐29‐oic acid) and its derivatives (13 species) revealed that the conformational features of these compounds in CDCl<jats:sub>3</jats:sub> solution depend on whether the functional groups at C‐29 are trigonal, such as COOCH<jats:sub>3</jats:sub>, or tetrahedral, such as CH<jats:sub>2</jats:sub>OH. In order to study the conformational features of these two groups of compounds, vicinal coupling constants between the protons on the E rings of the methyl ester of D : C‐friedoolean‐8‐en‐29‐oic acid, D : C‐friedoolean‐8‐en‐29‐oic and its acetate were measured. Comparison of the results with the steric geometries to be expected from the molecular mechanics calculation for the E‐ring moieties of these derivatives in the S form (D‐E rings: boat‐boat form) and the F form (D‐E rings: chair‐chair form) led to the conclusion that the compounds having a trigonal functional group at C‐29 mainly adopt the S form, and those having a tetrahedral functional group at C‐29 are present as mixtures of the S and F form in equilibrium in the solutions.</jats:p>

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