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Synlett 2010(2): 199-202  
DOI: 10.1055/s-0029-1218576
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Solution- and Solid-Phase Synthesis of Tetrahydroquinoline-Based Polycyclics Having α,β-Unsaturated γ-Lactam and δ-Lactone Functionalities

Shahriar Khadem*a,b, Konstantin A. Udachina, Prabhat Aryaa
a Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, ON, K1A 0R6, Canada
e-Mail: shahriar_khadem@hc-sc.gc.ca;
b Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, ON, K1N 6N5, Canada
Further Information

Publication History

Received 17 July 2009
Publication Date:
17 December 2009 (online)

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Abstract

With the goal of the library generation using the tetrahydroquinoline-based derivative, a simple and practical enantioselective synthesis of the tetrahydroquinoline derivatives having α,β-unsaturated γ-lactam and δ-lactone functional groups was achieved. The phenolic hydroxy group in the α,β-unsaturated γ-lactam was utilized as an anchoring site for the solid-phase synthesis. The ring-closing metathesis approach yielded the desired tricyclic products on the solid phase.

Key words

lactams - lactones - fused-ring systems - heterocycles - asymmetric synthesis - solid-phase synthesis

    References and Notes

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Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no CCDC 730001. Copies of the data can be obtained, free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 (1223)336033; or email: deposit@ccdc.cam.ac.uk].