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Synfacts 2009(10): 1096-1096
DOI: 10.1055/s-0029-1217930
DOI: 10.1055/s-0029-1217930
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Conjugated Ladder Systems by a Reductive Double Cyclization
H. Zhang, T. Karasawa, H. Yamada, A. Wakamiya, S. Yamaguchi*
Nagoya University, Japan
Further Information
Publication History
Publication Date:
22 September 2009 (online)
![](https://www.thieme-connect.de/media/synfacts/200910/lookinside/thumbnails/10.1055-s-0029-1217930-1.jpg)
Significance
The intramolecular cyclization of ortho-substituted benzene rings is a popular synthetic technique for the formation of benzene-fused five-membered rings. The authors have extended this technique to the synthesis of ladder-type polycyclic compounds by employing diaryl acetylene precursors. In previous reports, reduction of the acetylene moiety led to a double cyclization with heteroatoms. In the current paper, carbonyl substituents on the benzene ring act as the reducible moiety and are used to generate methylene-bridged stilbenes (2) and dibenzo[a,e]pentalenes (3).