Synthesis of 3-Alkyl- and 3-Chloroalkyl-2-hydroxybenzoates Based on [3+3] Cyclizations of 4-Alkyl- and 4-Chloroalkyl-1,3-bis(trimethylsilyloxy)buta-1,3-dienes

Van Thi Hong Nguyen; Esen Bellur; Bettina Appel; Peter Langer

doi:10.1055/s-2006-926381

PAPER

Synthesis of 3-Alkyl- and 3-Chloroalkyl-2-hydroxybenzoates Based on [3+3] Cyclizations of 4-Alkyl- and 4-Chloroalkyl-1,3-bis(trimethylsilyloxy)buta-1,3-dienes

Van Thi Hong Nguyen^a, Esen Bellur^a, Bettina Appel^a, Peter Langer*^b,c
^a Institut für Chemie und Biochemie, Universität Greifswald, Soldmannstr. 16, 17487 Greifswald, Germany
^b Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +381 4986412; e-Mail: peter.langer@uni-rostock.de;
^c Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany

Abstract

All articles of this category

Abstract

The TiCl₄-mediated [3+3] cyclization of 4-alkyl- and 4-chloroalkyl-1,3-bis(trimethylsilyloxy)buta-1,3-dienes with 3-silylalk-2-en-1-ones afforded 3-alkyl- and 3-chloroalkyl-2-hydroxybenzoates, respectively; the latter containing a remote chloride functionality. The TiCl₄- and TiBr₄-mediated [3+3] cyclization of 1,3-bis(trimethylsilyloxy)-4-chloroalkylbuta-1,3-dienes with 1,1-diacetylcyclopropane afforded salicylates containing two remote halide functionalities.

Key words

arenes - cyclizations - domino reactions - silyl enol ethers

Full Text

References

<A NAME="RT11605SS-1">1</A> Römpp Lexikon Naturstoffe Steglich W. Fugmann B. Lang-Fugmann S. Thieme; Stuttgart: 1997.

3-(n-Undecyl)-1,2-dihydroxybenzene:

<A NAME="RT11605SS-2A">2a</A> Miyakoshi T. Togashi H. Synthesis 1990, 407

<A NAME="RT11605SS-2B">2b</A> Asakawa Y. Masuya T. Tori M. Campbell EO. Phytochemistry 1987, 26: 735

3-(Pentadeca-8,11-dienyl)pyrocatechol:

<A NAME="RT11605SS-2C">2c</A> Sunthankar J. Dawson R. J. Am. Chem. Soc. 1954, 76: 5070

<A NAME="RT11605SS-2D">2d</A> Dawson R. Markiswitz J. J. Org. Chem. 1965, 30: 1610

<A NAME="RT11605SS-2E">2e</A> Adawadkar PD. Elsohly MA. Phytochemistry 1983, 22: 1280

Bhilawanol:

<A NAME="RT11605SS-2F">2f</A> Mason S. J. Am. Chem. Soc. 1945, 67: 418

5-Chlorflexirubin:

<A NAME="RT11605SS-2G">2g</A> Sargent MV. Wangchareontrakul S. J. Chem. Soc., Perkin Trans. 1 1989, 431

Belamcandol A:

<A NAME="RT11605SS-2H">2h</A> Fukuyama Y. Okino J. Kodama M. Chem. Pharm. Bull. 1991, 39: 1877

<A NAME="RT11605SS-2I">2i</A> Marner F.-J. Horper W. Helv. Chim. Acta 1992, 75: 1557

<A NAME="RT11605SS-2J">2j</A> Oshima R. Yamauchi Y. Watanabe C. Kumanotani J. J. Org. Chem. 1985, 50: 2613

<A NAME="RT11605SS-2K">2k</A> Budzikiewicz H. Scholl H. Neuenhaus W. Pulverer G. Korth H. Z. Naturforsch. B 1980, 35: 909

Amorfrutin B:

<A NAME="RT11605SS-2L">2l</A> Mitscher LA. Park YH. Al-Shamma A. Hudson PB. Haas T. Phytochemistry 1981, 20: 781

<A NAME="RT11605SS-2M">2m</A> Anaya AL. Mata R. Rivero-Cruz F. Hernandez-Bautista BE. Chavez-Velasco D. Gomez-Pompa A. J. Chem. Ecol. 1999, 25: 141

<A NAME="RT11605SS-2N">2n</A> Rivero-Cruz JF. Chavez D. Bautista BH. Anaya AL. Mata R. Phytochemistry 1997, 45: 1003

<A NAME="RT11605SS-2O">2o</A> Groweiss A. Cardellina JH. Pannell LK. Uyakul D. Kashman Y. Boyd MR. J. Nat. Prod. 1997, 60: 116

<A NAME="RT11605SS-2P">2p</A> David JM. Chavez JP. Chai H.-B. Pezzuto JM. Cordell GA. J. Nat. Prod. 1998, 61: 287

Hierridin B:

<A NAME="RT11605SS-2Q">2q</A> Jinno S. Hata K. Shimidzu N. Okita T. J. Antibiot. 1998, 51: 508

<A NAME="RT11605SS-2R">2r</A> Jinno S. Okita T. Chem. Pharm. Bull. 1998, 46: 1688

<A NAME="RT11605SS-2S">2s</A> Papendorf O. Koenig GM. Wright AD. Phytochemistry 1998, 49: 2383

<A NAME="RT11605SS-3">3</A> For a review of 1,3-bis(silyl) enol ethers, see: Langer P. Synthesis 2002, 441

<A NAME="RT11605SS-4A">4a</A> Chan T.-H. Brownbridge P. J. Am. Chem. Soc. 1980, 102: 3534

<A NAME="RT11605SS-4B">4b</A> Brownbridge P. Chan T.-H. Brook MA. Kang GJ. Can. J. Chem. 1983, 61: 688

<A NAME="RT11605SS-5A">5a</A> Nguyen VTH. Langer P. Tetrahedron Lett. 2005, 46: 815

<A NAME="RT11605SS-5B">5b</A> Bose G. Nguyen VTH. Ullah E. Lahiri S. Görls H. Langer P. J. Org. Chem. 2004, 69: 9128

For sequential [3+3] cyclization/Suzuki reactions, see:

<A NAME="RT11605SS-5C">5c</A> Nguyen VTH. Langer P. Tetrahedron Lett. 2005, 46: 1013

<A NAME="RT11605SS-6">6</A> Molander GA. Cameron KO. J. Am. Chem. Soc. 1993, 115: 830

Nguyen, V. T. H.; Bellur, E.; Appel, B.; Langer, P., unpublished results.

<A NAME="RT11605SS-8">8</A> Langer P. Bellur E. J. Org. Chem. 2003, 68: 9742

<A NAME="RT11605SS-9">9</A> For a review of dianions, see: Thompson CM. Green D. Tetrahedron 1991, 47: 4223

<A NAME="RT11605SS-10A">10a</A> Weiler L. J. Am. Chem. Soc. 1970, 92: 6702

<A NAME="RT11605SS-10B">10b</A> Sum P.-E. Weiler L. Can. J. Chem. 1977, 55: 996

<A NAME="RT11605SS-11">11</A> Lambert PH. Vaultier M. Carrié R. J. Org. Chem. 1985, 50: 5352