A Convenient Synthesis of Tetrasubstituted Furans from Propargylic Dithioacetals

Abstract

A convenient procedure for the regioselective synthesis of tetrasubstituted furans from the corresponding propargylic dithioacetals is described. Treatment of propargylic dithioacetals with n-BuLi and an aldehyde followed by mercuric acetate promoted annulation and desulfurization affords the corresponding mercurio-substituted furans. Subsequent replacement of the mercury moiety with iodine yields the corresponding 2,4,5-trisubstituted 3-iodofurans. Transition-metal-catalyzed cross-coupling reactions of the iodofurans furnish a variety of tetrasubstituted furans.

annulation - tetrasubstituted furan - propargylic dithioacetal - mercuric acetate - transition-metal-catalyzed cross-coupling

References and Notes

<A NAME="RW31905ST-1A">1a</A> Comprehensive Heterocyclic Chemistry   Katrizky AR. Rees CW. Scriven EFV. Pergamon; New York: 1996.  Vol. 2: 

<A NAME="RW31905ST-1B">1b</A> Comprehensive Heterocyclic Chemistry   Vol. 4:  Katrizky AR. Rees CW. Pergamon; New York: 1984. 

<A NAME="RW31905ST-1C">1c</A> Natural Products Chemistry   Nakanishi K. Goto T. Ito S. Natori S. Nozoe S. Kodansha; Tokyo: 1974.  Vol. 1-3: 

<A NAME="RW31905ST-1D">1d</A> Shipman M. Contemp. Org. Synth.  1995,  2:  1 

<A NAME="RW31905ST-2A">2a</A> The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications   Eicher T. Hauptmann S. Wiley-VCH; Weinheim: 2003. 

<A NAME="RW31905ST-2B">2b</A> Common Fragrance and Flavor Materials   Bauer K. Garbe D. VCH; Weinheim: 1985. 

<A NAME="RW31905ST-2C">2c</A> Vernin G. The Chemistry of Heterocyclic Flavouring and Aroma Compounds   Ellis Horwood; Chichester: 1982. 

<A NAME="RW31905ST-3A">3a</A> Maier M. In Organic Synthesis Highlights II   Waldmann H. VCH; Weinheim: 1995.  p.231 

<A NAME="RW31905ST-3B">3b</A> Comprehensive Organic Synthesis   Trost BM. Fleming I. Pergamon Press; Oxford: 1991. 

<A NAME="RW31905ST-3C">3c</A> Lipshutz BH. Chem. Rev.  1986,  86:  795 

For recent reviews, see:

<A NAME="RW31905ST-4A">4a</A> Hou XL. Cheung HY. Hon TY. Kwan PL. Lo TH. Tong SY. Wong HNC. Tetrahedron  1998,  54:  1955 

<A NAME="RW31905ST-4B">4b</A> Keay BA. Chem. Soc. Rev.  1999,  28:  209 

For recent reviews, see:

<A NAME="RW31905ST-5A">5a</A> Brown RCD. Angew. Chem. Int. Ed.  2005,  44:  850 

<A NAME="RW31905ST-5B">5b</A> Cacchi S. J. Organomet. Chem.  1999,  576:  42 

<A NAME="RW31905ST-6A">6a</A> Liu Y. Song F. Song Z. Liu M. Yan B. Org. Lett.  2005,  7:  5409 ; and references cited therein

<A NAME="RW31905ST-6B">6b</A> Liu Y. Song F. Cong L. J. Org. Chem.  2005,  70:  6999 

<A NAME="RW31905ST-6C">6c</A> Duan X.-h. Liu X.-y. Guo L.-n. Liao M.-c. Liu W.-M. Liang Y.-m. J. Org. Chem.  2005,  70:  6980 

<A NAME="RW31905ST-6D">6d</A> Sromek AW. Kel’in AV. Gevorgyan V. Angew. Chem. Int. Ed.  2004,  43:  2280 

<A NAME="RW31905ST-6E">6e</A> Ma S. Zhang J. Lu L. Chem. Eur. J.  2003,  9:  2447 ; and references cited therein

<A NAME="RW31905ST-6F">6f</A> Yavari I. Anary-Abbasinejad M. Alizadeh A. Tetrahedron Lett.  2002,  43:  4503 

<A NAME="RW31905ST-6G">6g</A> Aurrecoechea JM. Pérez E. Tetrahedron Lett.  2001,  42:  3839 

<A NAME="RW31905ST-6H">6h</A> Ma S. Zhang J. Chem. Commun.  2000,  117 

<A NAME="RW31905ST-6I">6i</A> Gabriele B. Salerno G. Lauria E. J. Org. Chem.  1999,  64:  7687 

<A NAME="RW31905ST-6J">6j</A> Iwasawa N. Ochiai T. Maeyama K. J. Org. Chem.  1998,  63:  3164 

<A NAME="RW31905ST-6K">6k</A> MaGee DI. Leach JD. Tetrahedron Lett.  1997,  38:  8129 

<A NAME="RW31905ST-6L">6l</A> Danheiser RL. Stoner EJ. Koyama H. Yamashita DS. Klade CA. J. Am. Chem. Soc.  1989,  111:  4407 

<A NAME="RW31905ST-7">7</A> For a recent review, see: Luh T.-Y. Lee C.-F. Eur. J. Org. Chem.  2005,  3875 

<A NAME="RW31905ST-8A">8a</A> Lee C.-F. Yang L.-M. Hwu T.-Y. Feng A.-H. Tseng J.-C. Luh T.-Y. J. Am. Chem. Soc.  2000,  122:  4992 

<A NAME="RW31905ST-8B">8b</A> Zhang L.-Z. Chen C.-W. Lee C.-F. Wu C.-C. Luh T.-Y. Chem. Commun.  2002,  2336 

<A NAME="RW31905ST-8C">8c</A> Lee C.-F. Liu C.-Y. Song H.-C. Luo S.-J. Tseng J.-C. Tso H.-H. Luh T.-Y. Chem. Commun.  2002,  2824 

<A NAME="RW31905ST-8D">8d</A> Liu C.-Y. Luh T.-Y. Org. Lett.  2002,  4:  4305 

<A NAME="RW31905ST-8E">8e</A> Tseng J.-C. Lin H.-C. Huang S.-L. Lin C.-L. Jin B.-Y. Chen C.-Y. Yu J.-K. Chou P.-T. Luh T.-Y. Org. Lett.  2003,  5:  4381 

<A NAME="RW31905ST-9">9</A> Bridges AJ. Thomas RD. J. Chem. Soc., Chem. Commun.  1984,  694 

<A NAME="RW31905ST-10A">10a</A> Fujita E. Nagao Y. Kaneko K. Chem. Pharm. Bull.  1978,  26:  3743 

<A NAME="RW31905ST-10B">10b</A> Lipshutz BH. Moretti R. Crow R. Tetrahedron Lett.  1989,  30:  15 

<A NAME="RW31905ST-11A">11a</A> Metal-Catalyzed Cross-Coupling Reactions   de Meijere A. Stang PJ. Wiley-VCH; Weinheim: 2004.  2nd ed: 

<A NAME="RW31905ST-11B">11b</A> Metal-Catalyzed Cross-Coupling Reactions   Diederich F. Stang PJ. Wiley-VCH; Weinheim: 1998. 

<A NAME="RW31905ST-12">12</A> Application of Transition Metal Catalysts in Organic Synthesis   Brandsma L. Vasilevsky SF. Verkruijsse HD. Springer-Verlag; Berlin/Heidelberg: 1999. 

<A NAME="RW31905ST-13">13</A> Tanabe Y. Wakimura K.-i. Nishii Y. Muroya Y. Synthesis  1996,  388