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Synthesis 2005(8): 1237-1244  
DOI: 10.1055/s-2005-865291
PAPER
© Georg Thieme Verlag Stuttgart · New York

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;
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Publikationsverlauf

Received 22 December 2004
Publikationsdatum:
07. April 2005 (online)

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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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7

This compund was obtained as a mixture of 11 and the product of the 1,2-reduction in a ratio of ca. 30:1.