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The Synthesis and Crystal Structure of (4α,8β,13β,16β)-13-Methyl-16,18-diol-17-Norkaurane: A Simultaneous Reduction Product of Isosteviol

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Abstract

(4α,8β,13β,16β)-13-methyl-16,18-diol-17-norkaurane was synthesized by esterification and reduction of isosteviol, respectively. The structure of the title compound was established by spectral analysis and X-ray diffraction studies. The compound crystallizes in the orthorhombic space group P212121 with unit cell parameters: a = 7.3705 (14) Å, b = 13.508 (3) Å, c = 20.139 (4) Å, V = 2005.1 (7) Å3, Z = 4. The conformation of rings A and B is chair, whereas the conformation of ring C is unsymmetrical distorted chair. The stereochemistry of the A/B and B/C ring junctions is trans, while the five-membered ring D adopts an envelope conformation.

Graphical Abstract

(4α,8β,13β,16β)-13-methyl-16,18-diol-17-norkaurane was synthesized by esterification and reduction of isosteviol, respectively. The structure of the title compound was established by spectral analysis and X-ray diffraction studies.

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Acknowledgments

We are grateful to the China Ministry of Health Foundation for Scientific Research (project No. WKJ2005-2-022) for financial support.

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Authors and Affiliations

  1. Institute of Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Southeast University, 210096, Nanjing, People’s Republic of China

    Junqing Chen, Min Sun, Jin Cai, Meng Cao, Wen Zhou & Min Ji

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  1. Junqing Chen
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  2. Min Sun
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  3. Jin Cai
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  4. Meng Cao
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  5. Wen Zhou
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  6. Min Ji
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Correspondence to Min Ji.

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Chen, J., Sun, M., Cai, J. et al. The Synthesis and Crystal Structure of (4α,8β,13β,16β)-13-Methyl-16,18-diol-17-Norkaurane: A Simultaneous Reduction Product of Isosteviol. J Chem Crystallogr 41, 519–522 (2011). https://doi.org/10.1007/s10870-010-9912-6

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  • DOI: https://doi.org/10.1007/s10870-010-9912-6

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