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Synthesis 2005(8): 1237-1244
DOI: 10.1055/s-2005-865291
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
Weitere Informationen
Received
22 December 2004
Publikationsdatum:
07. April 2005 (online)
Publikationsverlauf
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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This compund was obtained as a mixture of 11 and the product of the 1,2-reduction in a ratio of ca. 30:1.