title: 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.
authors: Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan. ktanino@sci.hokudai.ac.jp
authors: Keiji
authors: K
authors: Tanino
authors: Motomasa
authors: M
authors: Takahashi
authors: Yoshihide
authors: Y
authors: Tomata
authors: Hiroshi
authors: H
authors: Tokura
authors: Taketo
authors: T
authors: Uehara
authors: Takashi
authors: T
authors: Narabu
authors: Masaaki
authors: M
authors: Miyashita
references: J Org Chem. 2001 Jan 12;66(1):233-42
references: 11429905
references: Org Biomol Chem. 2003 Dec 21;1(24):4364-6
references: 14685306