A versatile and practical method for regioselective synthesis of polysubstituted furanonaphthoquinones.

An efficient and attractive synthesis of a series of novel poly-functionalized phosphorus zwitterions was achieved via three-component reactions of the corresponding functional nucleophiles, aldehydes, and Bu(3)P in the presence of acidic promoter. These polysubstituted zwitterions could regioselectively undergo further transformations to synthetically important furanonaphthoquinones and related products via the intramolecular Wittig reaction. These methods could have potential application in synthetic and pharmaceutical chemistry for its facilitation and easily accessible commercial materials.

[1]  Wenwei Lin,et al.  Preparation of functional benzofurans and indoles via chemoselective intramolecular Wittig reactions. , 2012, Chemical communications.

[2]  M. Davies-Coleman,et al.  Cytotoxic and antioxidant marine prenylated quinones and hydroquinones. , 2012, Natural product reports.

[3]  Wenwei Lin,et al.  Preparation of functional phosphorus zwitterions from activated alkanes, aldehydes, and tributylphosphine: synthesis of polysubstituted furo[3,2-c]coumarins. , 2012, Organic letters.

[4]  Wenwei Lin,et al.  Syntheses of furo[3,4-c]coumarins and related furyl coumarin derivatives via intramolecular Wittig reactions. , 2012, Organic & biomolecular chemistry.

[5]  C. Wiart,et al.  Reviews on 1,4-naphthoquinones from Diospyros L. , 2012, Journal of Asian natural products research.

[6]  J. Menéndez,et al.  A facile, three-component domino protocol for the microwave-assisted synthesis of functionalized naphtho[2,3-b]furan-4,9-diones in water , 2011 .

[7]  C. Freire,et al.  Synthesis and biological evaluation of substituted α- and β-2,3-dihydrofuran naphthoquinones as potent anticandidal agents , 2010 .

[8]  Wenwei Lin,et al.  Preparation of tetrasubstituted furans via intramolecular Wittig reactions with phosphorus ylides as intermediates. , 2010, Organic letters.

[9]  C. Tzeng,et al.  Furo[3',2':3,4]naphtho[1,2-d]imidazole derivatives as potential inhibitors of inflammatory factors in sepsis. , 2009, Bioorganic & medicinal chemistry.

[10]  D. MacMillan,et al.  The advent and development of organocatalysis , 2008, Nature.

[11]  M. Teimouri,et al.  An efficient three-component reaction involving [3 + 1 + 1] furannulation leading to furanonaphthoquinones in water , 2008 .

[12]  S. Mukherjee,et al.  Asymmetric enamine catalysis. , 2007, Chemical reviews.

[13]  A. Tanaka,et al.  Cytotoxic Activity toward KB Cells of 2-Substituted Naphtho[2,3-b]furan-4,9-diones and Their Related Compounds , 2006, Bioscience, biotechnology, and biochemistry.

[14]  K. Jørgensen,et al.  A general organocatalyst for direct alpha-functionalization of aldehydes: stereoselective C-C, C-N, C-F, C-Br, and C-S bond-forming reactions. Scope and mechanistic insights. , 2005, Journal of the American Chemical Society.

[15]  Y. Hayashi,et al.  Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes. , 2005, Angewandte Chemie.

[16]  D. V. Davydov,et al.  Synthesis of Naphtho[2,3-b]furan-4,9-diones Having a Trifluoromethyl Group under Conditions of Phase-Transfer Catalysis , 2004 .

[17]  D. Hollomon,et al.  Mode of action and pesticidal activity of the natural product dunnione and of some analogues. , 2003, Pest management science.

[18]  Y. R. Lee,et al.  FACILE SYNTHESIS OF AVICEQUINONE-B NATURAL PRODUCT , 2002 .

[19]  A. Tanaka,et al.  Nucleophilic substitutions of 2-chloronaphtho[2,3-b]furan-4,9-dione with amines , 1998 .

[20]  A. Tanaka,et al.  Nucleophilic Substitutions of 2-Halonaphtho[2, 3-b]furan-4, 9-diones and 2-Nitronaphtho[2, 3-b]furan-4, 9-dione , 1997 .

[21]  Kazuhiro Kobayashi,et al.  One-pot synthesis of naphtho[2,3-b]furan-4,9-diones by sequential coupling/ring closure reactions , 1997 .

[22]  K. Lee,et al.  Antitumor agents. 89. Psychorubrin, a new cytotoxic naphthoquinone from Psychotria rubra and its structure-activity relationships. , 1987, Journal of medicinal chemistry.