New construction of the bicyclo[3.3.1]nonane system via Lewis acid promoted regioselective ring-opening reaction of the tricyclo[4.4.0.0 5,7]dec-2-ene derivative

A new access to the bicyclo[3.3.1]nonane system, which is a common structure in a number of polyisoprenylated phloroglucinol derivatives (phloroglucins), has been developed via the Lewis acid promoted regioselective ring-opening reaction of the cyclopropane, a tricyclo[4.4.0.0 5,7]dec-2-ene derivati...

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Bibliographic Details
Published inTetrahedron letters Vol. 47; no. 36; pp. 6347 - 6351
Main Authors Abe, Masahito, Nakada, Masahisa
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 04.09.2006
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FLORAL RESINS
PHLOROGLUCINOL DERIVATIVES
POLYCYCLIC POLYPRENYLATED ACYLPHLOROGLUCINOLS
2 POLYISOPRENYLATED BENZOPHENONES
GARCINIA-SUBELLIPTICA
HYPERICUM-PERFORATUM L
BETA-KETO SULFONES
ST-JOHNS-WORT
PRENYLATED BENZOPHENONE DERIVATIVES
GARSUBELLIN-A
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Summary:A new access to the bicyclo[3.3.1]nonane system, which is a common structure in a number of polyisoprenylated phloroglucinol derivatives (phloroglucins), has been developed via the Lewis acid promoted regioselective ring-opening reaction of the cyclopropane, a tricyclo[4.4.0.0 5,7]dec-2-ene derivative.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.07.010