Stereocontrolled Synthesis of the Oxabicyclo[2.2.1]heptane Segment of Solanoeclepin A

Shingo Tojo; Minoru Isobe

doi:10.1055/s-2005-865291

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Stereocontrolled Synthesis of the Oxabicyclo[2.2.1]heptane Segment of Solanoeclepin A

Shingo Tojo, Minoru Isobe*
Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan
Fax: +81(52)7894111; e-Mail: isobem@agr.nagoya-u.ac.jp;

Abstract

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Abstract

An asymmetric synthesis of the oxabicyclo[2.2.1]heptane segment of Solanoeclepin A, which shows significant hatch-stimulating activity for the potato cyst nematode, is described. The oxabicyclo framework was constructed by iodoetherification with bis(collidine)iodine(I) hexafluorophosphate in acetonitrile. The oxabicyclo segment was further synthesized by the following stereoselective dihydroxylation and dimethyl group introduction.

Key words

solanoeclepin A - hatch-stimulating activity - oxabicyclo[2.2.1]heptane - iodoetherification

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References

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