Convenient Synthesis of Polysubstituted 3-Iodofurans through the Tandem Ring-Opening/Cyclization Reaction of 1-Alkynyl-2,3-epoxy Alcohols

Shu-guang Wen; Wei-min Liu; Yong-min Liang

doi:10.1055/s-2007-990830

PAPER

Convenient Synthesis of Polysubstituted 3-Iodofurans through the Tandem Ring-Opening/Cyclization Reaction of 1-Alkynyl-2,3-epoxy Alcohols

Shu-guang Wen^a,b, Wei-min Liu^a, Yong-min Liang*^a,c
^a State Key Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China
^b Graduate School of Chinese Academy of Sciences, Beijing 100039, P. R. of China
^c State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: liangym@lzu.edu.cn;

Abstract

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Abstract

A novel method for the synthesis of highly substituted iodine-containing furans has been developed by the cyclization of 1-(arylethynyl)-2,3-epoxy alcohols (1-aryl-4,5-epoxyalk-1-yn-3-ols) with alcohols as nucleophiles under very mild reaction conditions. The resulting iodine-containing furans can be readily elaborated to more complex products using known organopalladium chemistry.

Key word

iodofuran - tandem reaction - epoxide - electrophilic cyclization

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References

<A NAME="RF13107SS-1A">1a</A> Katritzky AR. Advances in Heterocyclic Chemistry Academic Press; New York: 1982.

<A NAME="RF13107SS-1B">1b</A> Sargent MV. Dean FM. In Comprehensive Heterocyclic Chemistry Vol. 4: Katritzky AR. Rees CW. Pergamon Press; New York: 1984. p.599-656

<A NAME="RF13107SS-1C">1c</A> Nakanishi K. Natural Products Chemistry Kodansha; Tokyo: 1974.

<A NAME="RF13107SS-1D">1d</A> Bird CW. Cheeseman GWH. In Comprehensive Heterocyclic Chemistry Vol. 4: Katritzky AR. Rees CW. Pergamon; New York: 1984.

<A NAME="RF13107SS-2">2</A> For pharmaceuticals, see, for example: Mortensen DS. Rodrigues AL. Karlson KE. Sun J. Katzenellenbogen BS. Katzenellenbogen JA. J. Med. Chem. 2001, 44: 3838

Recent reviews:

<A NAME="RF13107SS-3A">3a</A> Hou XL. Yang Z. Wong HNC. In Progress in Heterocyclic Chemistry Vol. 14: Gribble GW. Gilchrist TL. Pergamon Press; Oxford: 2002. p.139-179

<A NAME="RF13107SS-3B">3b</A> Cacchi S. J. Organomet. Chem. 1999, 576: 42-64

<A NAME="RF13107SS-3C">3c</A> Hou XL. Cheung HY. Hon TY. Kwan PL. Lo TH. Tong SY. Wong HNC. Tetrahedron 1998, 54: 1955

<A NAME="RF13107SS-4">4</A> Brown RCD. Angew. Chem. Int. Ed. 2005, 44: 850

<A NAME="RF13107SS-5A">5a</A> Sheng H. Lin S. Huang Y. Tetrahedron Lett. 1986, 27: 4893

<A NAME="RF13107SS-5B">5b</A> Fukuda Y. Shiragami H. Utimoto K. Nozaki H. J. Org. Chem. 1991, 56: 5816

<A NAME="RF13107SS-5C">5c</A> Kel’in AV. Gevorgyan V. J. Org. Chem. 2002, 67: 95

<A NAME="RF13107SS-5D">5d</A> Ma S. Zhang J. Chem. Commun. 2000, 117

<A NAME="RF13107SS-5E">5e</A> Hashmi ASK. Schwarz L. Choi J.-H. Frost TM. Angew. Chem. Int. Ed. 2000, 39: 2285

<A NAME="RF13107SS-5F">5f</A> Marshall JA. Wang X.-J. J. Org. Chem. 1991, 56: 960

<A NAME="RF13107SS-5G">5g</A> Marshall JA. Bartley GS. J. Org. Chem. 1994, 59: 7169

<A NAME="RF13107SS-6A">6a</A> Wakabayashi Y. Fukuda Y. Shiragami H. Utimoto K. Nozaki H. Tetrahedron 1985, 41: 3655

<A NAME="RF13107SS-6B">6b</A> Gabriele B. Salerno G. Lauria E. J. Org. Chem. 1999, 64: 7687

<A NAME="RF13107SS-6C">6c</A> Seiller B. Bruneau C. Dixneuf PH. J. Chem. Soc., Chem. Commun. 1994, 493

<A NAME="RF13107SS-6D">6d</A> Seiller B. Bruneau C. Dixneuf PH. Tetrahedron 1995, 51: 13089

<A NAME="RF13107SS-7A">7a</A> Lo C.-Y. Guo H. Lian J.-J. Shen F.-M. Liu R.-S. J. Org. Chem. 2002, 67: 3930

<A NAME="RF13107SS-7B">7b</A> Marshall JA. DuBay WJ. J. Am. Chem. Soc. 1992, 114: 1450

<A NAME="RF13107SS-7C">7c</A> Hashmi ASK. Sinha P. Adv. Synth. Catal. 2004, 346: 432

<A NAME="RF13107SS-8">8</A> Arcadi A. Cacchi S. Fabrizi G. Marinelli F. Moro L. Synlett 1999, 1432

<A NAME="RF13107SS-9">9</A> Arcadi A. Cacchi S. Di Giuseppe S. Fabrizi G. Marinelli F. Org. Lett. 2002, 4: 2409

<A NAME="RF13107SS-10A">10a</A> El-Taeb GMM. Evans AB. Jones S. Knight DW. Tetrahedron Lett. 2001, 42: 5945

<A NAME="RF13107SS-10B">10b</A> Bew SP. Knight DW. Chem. Commun. 1996, 1007

<A NAME="RF13107SS-11">11</A> Schultz-Fademrecht C. Zimmermann M. Fröhlich R. Hoppe D. Synlett 2003, 1969

<A NAME="RF13107SS-12A">12a</A> Chinchilla R. Najera C. Yus M. Chem. Rev. 2004, 104: 2667

<A NAME="RF13107SS-12B">12b</A> Tanabe Y. Wakimura K. Nishii Y. Muroya Y. Synthesis 1996, 388

For C-C bond formation, see:

<A NAME="RF13107SS-12C">12c</A> Lin S.-Y. Chen C.-L. Lee Y.-J. J. Org. Chem. 2003, 68: 2968

<A NAME="RF13107SS-12D">12d</A> Bach T. Krüger L. Eur. J. Org. Chem. 1999, 2045

For C-N bond formation, see:

<A NAME="RF13107SS-12E">12e</A> Hooper MW. Utsunomiya M. Hartwig JF. J. Org. Chem. 2003, 68: 2861

<A NAME="RF13107SS-12F">12f</A> Padwa A. Crawford KR. Rashatasakhon P. Rose M. J. Org. Chem. 2003, 68: 2609

For C-S bond formation, see:

<A NAME="RF13107SS-12G">12g</A> Arroyo Y. Rodriguez JF. Sanz-Tejedor MA. Santos M. Tetrahedron Lett. 2002, 43: 9129

<A NAME="RF13107SS-13">13</A> Eicher T. Hauptmann S. Speicher A. The Chemistry of Heterocycles 2nd ed.: Wiley-VCH; Weinheim: 2003. p.52-62

<A NAME="RF13107SS-14">14</A> Boger DL. Modern Organic Synthesis TSRI Press; La Jolla: 1999. p.45-48