Syntheses of macrocyclic bisbibenzyls on solid support

We describe a route for the polymer supported total synthesis of the cyclic bisbibenzyls of the isoplagiochin type found in liverworts. TentaGel® resins were used as solid support for a sequence involving Suzuki, Wittig and hydrogenation protocols. The polymer linked intermediates could be character...

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Bibliographic Details
Published inTetrahedron Vol. 61; no. 49; pp. 11692 - 11696
Main Authors Speicher, Andreas, Backes, Timo, Grosse, Stefan
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 05.12.2005
Elsevier
Subjects
Bisbibenzyls
Chemistry
Chemistry, Organic
HR-MAS NMR
Macrocycles
Physical Sciences
Science & Technology
Solid phase synthesis
TentaGel
TentaGel
Solid phase synthesis
HR-MAS NMR
Macrocycles
Bisbibenzyls
ORGANIC-SYNTHESIS
solid phase synthesis
BIBENZYLS
ISOPLAGIOCHIN-C
RESINS
bisbibenzylg
LIVERWORTS
PEPTIDES
macrocycles
CHEMISTRY
BAZZANIA-TRILOBATA
TemaGel
BIS(BIBENZYLS)
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Summary:We describe a route for the polymer supported total synthesis of the cyclic bisbibenzyls of the isoplagiochin type found in liverworts. TentaGel® resins were used as solid support for a sequence involving Suzuki, Wittig and hydrogenation protocols. The polymer linked intermediates could be characterized by HR-MAS NMR. This route is to be extended to the synthesis of small libraries of differently halogenated derivatives. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.09.048