Synthesis 2011(5): 759-763  
DOI: 10.1055/s-0030-1258415
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereospecific Synthesis of trans-5,6-Dihydropyridinones

Shang-Shing P. Chou*, Tsung-Han Yang, Wan-Shiuan Wu, Tzu-Han Chiu
Department of Chemistry, Fu Jen Catholic University, Taipei 24205, Taiwan, R. O. C.
Fax: +886(2)29023209; e-Mail: 002181@mail.fju.edu.tw ;
Further Information

Publication History

Received 15 December 2010
Publication Date:
21 January 2011 (online)

Abstract

An efficient synthesis of trans-5,6-dihydropyridinones bearing a heteroatom (Br, OH) at C-5 has been achieved. The formal synthesis of (±)-epiquinamide and (±)-homopumiliotoxin 223G has also been accomplished through the formation of (±)-trans-1-hydroxyquinolizidin-4-one.

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Crystallographic data (excluding structure factors) for compounds 4, 5, 6, 10, 11, and 12 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC 796324-796329 as well as their corresponding CIF files. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].