Stereoselective cyclization of stilbene derived carbocations

Cyclodimerization of 2,6-dimethoxy-4-methylstilbene under acidic conditions affords the rotationally restricted 1,3-bis-(2,6-dimethoxy-4-methylphenyl)-2-phenyl-1,2,3,4-tetrahydronaphthalene. Nucleophilic addition of this stilbene to 1,4-benzoquinone and maleic anhydride, respectively, followed by an...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron Vol. 59; no. 9; pp. 1501 - 1507
Main Authors Li, Xing-Cong, Ferreira, Daneel
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 24.02.2003
Elsevier
Subjects
butanolide
Chemistry
Chemistry, Organic
dihydrobenzofuran
Physical Sciences
Science & Technology
stereoselective cyclization
stilbene
tetrahydronaphthalene
stilbene
butanolide
stereoselective cyclization
dihydrobenzofuran
tetrahydronaphthalene
RESVERATROL
OLIGOSTILBENES
ROOTS
OLIGOMERIC STILBENES
Online AccessGet full text

Cover

More Information
Summary:Cyclodimerization of 2,6-dimethoxy-4-methylstilbene under acidic conditions affords the rotationally restricted 1,3-bis-(2,6-dimethoxy-4-methylphenyl)-2-phenyl-1,2,3,4-tetrahydronaphthalene. Nucleophilic addition of this stilbene to 1,4-benzoquinone and maleic anhydride, respectively, followed by an intramolecular cyclization yields dihydrobenzofuran derivatives and a trisubstituted butanolide, respectively. These stereoselective cyclizations involving stilbene derived carbocations apparently biomimic the cyclization of naturally occurring stilbenes during oxidative oligomerization. 2,6-Dimethoxy-4-methylstilbene is subject to facile transformation into a 1,2,3-trisubstituted tetrahydro-naphthalene derivative under acidic conditions. Similar reactions in the presence of 1,4-benzoquinone and maleic anhydride lead to the formation of dihydrobenzofuran and butanolide derivatives, respectively.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(03)00050-4