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Synthesis 2004(16): 2685-2691  
DOI: 10.1055/s-2004-831234
PAPER
© Georg Thieme Verlag Stuttgart · New York

The Synthesis of Tetrahydroquinolines Related to Virantmycin

Craig L. Francis, Natalie M. Williamson, A. David Ward*
Department of Chemistry, University of Adelaide, Adelaide, S.A. 5005, Australia
Fax: +61(8)83034358; e-Mail: david.ward@adelaide.edu.au;
Further Information

Publication History

Received 21 June 2004
Publication Date:
22 September 2004 (online)

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Abstract

4-Substituted anilines react with 1-methoxymethyl-1-butyl-3-trimethysilylpropargyl chloride but not with 1,1-dibutyl-3-trimethylsilylpropargyl chloride, to form the corresponding substituted N-propargylanilines. These anilines cyclise, using cuprous chloride, in the presence of trifluoroacetic anhydride, and, when the aniline substituent is electron donating, to give 6-substituted 2-butyl-2-methoxymethyl-1-trifluoroacetyl-1,2-dihydroquinolines. Chlorination, followed by selective dechlorination using sodium cyanoborohydride, of the 6-methyl product yields 2-butyl-2-methoxymethyl-3-chloro-6-methyl-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline which has the same relative stereochemistry as that in the antiviral compound, Virantmycin.

Key words

quinolines - diastereoselectivity - cyclisations - alkyl halides - alkynes - antiviral agents