Issue 10, 2011
From the journal:

Chemical Communications

Diastereoselective synthesis of the indeno-tetrahydropyridine core bearing a diaryl-substituted stereogenic quaternary carbon center of haouamine B†

Takeshi Tanaka,a   Hiromi Inui,a   Hiroshi Kida,a   Takeshi Kodama,a   Takuya Okamoto,a   Aki Takeshima,a   Yoshimitsu Tachia  and  Yoshiki Morimoto*a  

* Corresponding authors

a Department of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, Japan
E-mail: morimoto@sci.osaka-cu.ac.jp
Fax: +81 6 6605 2522
Tel: +81 6 6605 3141

Abstract

The characteristic indeno-tetrahydropyridine core of cytotoxic haouamine B (2) was efficiently synthesized featuring the diastereoselective construction of a diaryl-substituted stereogenic quaternary center by an intramolecular Pd-catalyzed α-C-arylation and subsequent direct conversion of the vinylogous imide function into the C2–C25 double bond by TsNHNH2.

Graphical abstract: Diastereoselective synthesis of the indeno-tetrahydropyridine core bearing a diaryl-substituted stereogenic quaternary carbon center of haouamine B

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Article information

DOI
https://doi.org/10.1039/C0CC04453A
Article type
Communication
Submitted
16 Oct 2010
Accepted
14 Dec 2010
First published
17 Jan 2011

Chem. Commun., 2011,47, 2949-2951

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Diastereoselective synthesis of the indeno-tetrahydropyridine core bearing a diaryl-substituted stereogenic quaternary carbon center of haouamine B

T. Tanaka, H. Inui, H. Kida, T. Kodama, T. Okamoto, A. Takeshima, Y. Tachi and Y. Morimoto, Chem. Commun., 2011, 47, 2949 DOI: 10.1039/C0CC04453A

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