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Total synthesis of solanoeclepin A

Nature Chemistry volume 3, pages 484–488 (2011)Cite this article

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Abstract

Cyst nematodes are troublesome parasites that live on, and destroy, a range of important host vegetable plants. Damage caused by the potato cyst nematode has now been reported in over 50 countries. One approach to eliminating the problem is to stimulate early hatching of the nematodes, but key hatching stimuli are not naturally available in sufficient quantities to do so. Here, we report the first chemical synthesis of solanoeclepin A, the key hatch-stimulating substance for potato cyst nematode. The crucial steps in our synthesis are an intramolecular cyclization reaction for construction of the highly strained tricyclo[5.2.1.01,6]decane skeleton (DEF ring system) and an intramolecular Diels–Alder reaction of a furan derivative for the synthesis of the ABC carbon framework. The present synthesis has the potential to contribute to addressing one of the critical food issues of the twenty-first century.

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Figure 1: Cyst nematodes and their effect on crops.
Figure 2: Stereoselective synthesis of right-hand segment 17.
Figure 3: Stereoselective synthesis of the heptacyclic compound 27.
Figure 4
Figure 5: Hatching stimulation effect of synthetic solanoeclepin A on G. rostochiensis.

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Acknowledgements

The authors thank Prof. T. Inabe (Hokkaido University) for X-ray diffraction measurements. This research was partly supported by the Global COE Program (project no. B01: Catalysis as the basis for innovation in materials science) and a Grant-in-Aid for Scientific Research on Innovative Areas (project no. 2105: Organic synthesis based on reaction integration) from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.

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Authors and Affiliations

  1. Faculty of Science, Hokkaido University, Sapporo, 060-0810, Japan

    Keiji Tanino, Motomasa Takahashi, Yoshihide Tomata & Hiroshi Tokura

  2. National Agriculture Research Center for Hokkaido Region, Sapporo, 062-8555, Japan

    Taketo Uehara & Takashi Narabu

  3. Faculty of Engineering, Kogakuin University, Hachioji, Tokyo, 192-0015, Japan

    Masaaki Miyashita

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  1. Keiji Tanino
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  3. Yoshihide Tomata
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  4. Hiroshi Tokura
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  7. Masaaki Miyashita
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Contributions

K.T. and M.M. conceived the experiments and analysed the results. M.T., Y.T. and H.T. performed the laboratory experiments and optimized the reaction conditions. T.U. and T.N. performed biological testing and evaluation of synthetic solanoeclepin A. K.T. and M.M. wrote the paper.

Corresponding authors

Correspondence to Keiji Tanino or Masaaki Miyashita.

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The authors declare no competing financial interests.

Supplementary information

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Supplementary information (PDF 7749 kb)

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Crystallographic data for compound 35 (CIF 38 kb)

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Crystallographic data for compound S18 (CIF 23 kb)

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Tanino, K., Takahashi, M., Tomata, Y. et al. Total synthesis of solanoeclepin A. Nature Chem 3, 484–488 (2011). https://doi.org/10.1038/nchem.1044

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