Synthesis of the Right-Hand Substructure of Solanoeclepin A

A synthesis of the right‐hand substructure 7 of solanoeclepin A (1), the most active natural hatching agent of potatocyst nematodes, was approached by an intramolecular [2+2] photocycloaddition. The construction of the strained bicyclo[2.1.1]hexane skeleton was achieved in five steps from dioxenone...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2001; no. 12; pp. 2371 - 2377
Main Authors Brière, Jean-François, Blaauw, Richard H., Benningshof, Jorg C. J., van Ginkel, Angeline E., van Maarseveen, Jan H., Hiemstra, Henk
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag GmbH 01.06.2001
WILEY‐VCH Verlag GmbH
Wiley
Subjects
Chemistry
Chemistry, Organic
Cyclization
Cycloaddition
Natural products
Photochemistry
Physical Sciences
Science & Technology
OXIDATION
natural products
cycloaddition
LIGANDS
photochemistry
ALLYLIC ALCOHOLS
CYCLOPROPANATION
cyclization
DERIVATIVES
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Summary:A synthesis of the right‐hand substructure 7 of solanoeclepin A (1), the most active natural hatching agent of potatocyst nematodes, was approached by an intramolecular [2+2] photocycloaddition. The construction of the strained bicyclo[2.1.1]hexane skeleton was achieved in five steps from dioxenone 9. A Simmons−Smith cyclopropanation enabled the installation of the required cyclopropane. Finally, a TPAP oxidation allowed the smooth formation of the strained cyclobutanone moiety.
Bibliography:istex:1B1B94436271B78D0C191549EA3DE9152E48C1A5
ark:/67375/WNG-QWNJSKXR-G
ArticleID:EJOC2371
ISSN:1434-193X
1099-0690
DOI:10.1002/1099-0690(200106)2001:12<2371::AID-EJOC2371>3.0.CO;2-O