Total synthesis of solanoeclepin A

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. The first chemical synthesis of solanoeclepin A is described. The novel 5-4-6-7-5-5 polycyclic architecture was constructed in a stereoselective manner via a cyclopentene annulation strategy, the intramolecular cyclization of an epoxy nitrile intermediate, and an intramolecular Diels–Alder reaction of a furan derivative.

Cite this article

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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