Citation
Jf. Briere et al., Synthesis of the right-hand substructure of solanoeclepin A, EUR J ORG C, (12), 2001, pp. 2371-2377
Citations number
23
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X
→ ACNP
Issue
12
Year of publication
2001
Pages
2371 - 2377
Database
ISI
SICI code
1434-193X(200106):12<2371:SOTRSO>2.0.ZU;2-H
Abstract
A synthesis of the right-hand substructure 7 of solanoeclepin A (1), the mo
st active natural hatching agent of potatocyst nematodes, was approached by
an intramolecular [2+2] photocycloaddition. The construction of the strain
ed bicyclo[2.1.1]hexane skeleton was achieved in five steps from dioxenone
9. A Simmons-Smith cyclopropanation enabled the installation of the require
d cyclopropane. Finally, a TPAP oxidation allowed the smooth formation of t
he strained cyclobutanone moiety.