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Synfacts 2006(4): 0402-0402  
DOI: 10.1055/s-2006-932083
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Solid-Phase Approach to Tetrahydroquinolones

Contributor(s): Yasuhiro Uozumi, Toshimasa Suzuka
K. L. Turner, T. M. Baker, S. Islam, D. J. Procter*, M. Stefaniak
University of Manchester and Pfizer Global Research & Development, Sandwich, UK
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Publication History

Publication Date:
24 March 2006 (online)

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Significance

Tetrahydroquinolone 5 was prepared via several steps starting from aryl halide 1 anchored on a benzyl thiol resin. Thus, the reaction of aryl halide 1 with a benzyl thiol resin gave the S-anchored product 2. The microwave-assisted Heck reaction of 2 with tert-butyl acrylate gave tert-butyl cinnamate 3. Oxidation of 3 with oxone in DMF followed by the Michael cyclization with K2CO3 gave the desired compound 4, bound to a resin. Tetrahydroquinolone 5a was readily isolated via SmI2-mediated cleavage from the resin-supported tetrahydroquinolone 4a in 15% yield over five steps.