The Synthesis of Tetrahydroquinolines Related to Virantmycin

Craig L. Francis; Natalie M. Williamson; A. David Ward

doi:10.1055/s-2004-831234

PAPER

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;

Abstract

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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

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References

<A NAME="RP06304SS-1A">1a</A> Williamson NM. March DR. Ward AD. Tetrahedron Lett. 1995, 36: 7721

<A NAME="RP06304SS-1B">1b</A> Raner KD. Skelton BW. Ward AD. White AH. Aust. J. Chem. 1990, 43: 609

<A NAME="RP06304SS-1C">1c</A> Raner KD. Ward AD. Aust. J. Chem. 1991, 44: 1749

<A NAME="RP06304SS-1D">1d</A> De Silva AN. Francis CL. Ward AD. Aust. J. Chem. 1993, 46: 1657

<A NAME="RP06304SS-1E">1e</A> Francis CL. Ward AD. Aust. J. Chem. 1994, 47: 2109

<A NAME="RP06304SS-1F">1f</A> Williamson NM. Ward AD. Tetrahedron 2004, in press

<A NAME="RP06304SS-2A">2a</A> Omura S. Nakagawa A. Hashimoto H. Oiwa R. Iwai Y. Hirano A. Shibukawa N. Kojima Y. J. Antibiot. 1980, 33: 1395

<A NAME="RP06304SS-2B">2b</A> Nakagawa A. Omura S. Tetrahedron Lett. 1981, 22: 2199

<A NAME="RP06304SS-2C">2c</A> Nakagawa A. Iwai Y. Hashimoto H. Miyazaki N. Oiwa R. Takahashi Y. Hirano A. Shibukawa N. Kojima Y. Omura S. J. Antibiot. 1981, 34: 1408

<A NAME="RP06304SS-2D">2d</A> Hill ML. Raphael RA. Tetrahedron 1990, 46: 4587

<A NAME="RP06304SS-2E">2e</A> Morimoto Y. Oda K. Shirahama H. Matsumoto T. Omura S. Chem. Lett. 1988, 6: 909

<A NAME="RP06304SS-2F">2f</A> Pearce CM. Sanders JKM. J. Chem. Soc., Perkin Trans. 1 1990, 409

<A NAME="RP06304SS-2G">2g</A> Morimoto Y. Shirahama H. Tetrahedron 1996, 52: 10631

<A NAME="RP06304SS-3">3</A> Cooper MA. Lucas MA. Taylor JM. Ward AD. Williamson NM. Synthesis 2001, 621

<A NAME="RP06304SS-4">4</A> Normant J.-F. Cahiez G. In Modern Synthetic Methods Vol. 3: Springer; New York: 1983. p.173

<A NAME="RP06304SS-5">5</A> Jorgensen MJ. Org. React. 1970, 18: 1

<A NAME="RP06304SS-6">6</A> Stadlwieser J. Synthesis 1985, 490

<A NAME="RP06304SS-7">7</A> Gauthier R. Axiotis GP. Chastrette M. J. Organomet. Chem. 1977, 140: 245

<A NAME="RP06304SS-8">8</A> Kotsuki H. Shimanouchi T. Ohshima R. Fujiwara S. Tetrahedron 1998, 54: 2709

<A NAME="RP06304SS-9">9</A> Crich D. Beckwith ALJ. Chen C. Yao Q. Davison IGE. Longmore RW. de Parrodi CA. Quintero-Cortes L. Sandoval-Ramirez J. J. Am. Chem. Soc. 1995, 117: 8757

<A NAME="RP06304SS-10">10</A> Holmes AB. Sporikou CN. Org. Synth. 1987, 65: 61