Synthetic Studies of Naphtho[2,3-b]furan Moiety Present in Diverse Bioactive Natural Products
Affiliation(s)
1 Department of Chemistry, Prabhat Kumar College, Contai, India. 2 Department of Chemistry, Indian Institute of Technology, Kharagpur, India.
1 Department of Chemistry, Prabhat Kumar College, Contai, India. 2 Department of Chemistry, Indian Institute of Technology, Kharagpur, India.
ABSTRACT
The preparation of several functionalized furan derivatives and attempts to transform them into a derivative containing 6H-furo[3,4-b]furanone skeleton towards the construction of naphtho[2,3-b] furan are described. Attempted Pummerer reaction of a furan sulfoxide derivative produced four interesting furan derivatives. Base promoted annulation between methyl 2-(phenylsulfinylmethyl)-3-furoate and 2-cyclohexenone proceeded to give dihydro naphtho[2,3-b]furanone derivative in a regiospecific manner.
The preparation of several functionalized furan derivatives and attempts to transform them into a derivative containing 6H-furo[3,4-b]furanone skeleton towards the construction of naphtho[2,3-b] furan are described. Attempted Pummerer reaction of a furan sulfoxide derivative produced four interesting furan derivatives. Base promoted annulation between methyl 2-(phenylsulfinylmethyl)-3-furoate and 2-cyclohexenone proceeded to give dihydro naphtho[2,3-b]furanone derivative in a regiospecific manner.
KEYWORDS
6H-Furo[3, 4-b]furanone, Naphtho[2, 3-b]furan, Intramolecular Pummerer Reaction, Desulfanylation, Lactonization
6H-Furo[3, 4-b]furanone, Naphtho[2, 3-b]furan, Intramolecular Pummerer Reaction, Desulfanylation, Lactonization
Cite this paper
Senapati, B. and Mal, D. (2015) Synthetic Studies of Naphtho[2,3-b]furan Moiety Present in Diverse Bioactive Natural Products. International Journal of Organic Chemistry, 5, 63-74. doi: 10.4236/ijoc.2015.52008.
Senapati, B. and Mal, D. (2015) Synthetic Studies of Naphtho[2,3-b]furan Moiety Present in Diverse Bioactive Natural Products. International Journal of Organic Chemistry, 5, 63-74. doi: 10.4236/ijoc.2015.52008.
References
[1] Lin, K.I., Su, J.C., Chien, C.M., Tseng, C.H., Chen, Y.L., Chang, L.S. and Lin, S.R. (2010) Naphtho[1,2-b]furan-4,5- dione Induces Apoptosis and S-Phase Arrest of MDA-MB-231 Cells through JNK and ERK Signaling Activation. Toxicology in Vitro, 24, 61-70.
http://dx.doi.org/10.1016/j.tiv.2009.09.002
Ito, C., Katsuno, S., Kondo, Y., Tan, H.T.W. and Fu-rukawa, H. (2000) Chemical Constituents of Avicennia Alba. Isolation and Structural Elucidation of New Naphthoquinones and Their Analogues. Chemical & Pharmaceutical Bulletin, 48, 339-343.
Hirai, K., Koyama, J., Pan, J., Simamura, E., Shimada, H. and Yamori, T. (1999) Cancer Detection and Prevention, 23, 539-550.
Nagata, K., Hirai, K., Koyama, J., Wada, Y. and Tamura, T. (1998) Antimicrobial Agents and Chemotherapy, 42, 700-702.
Takegami, T., Simamura, E., Hirai, K. and Koyama, J. (1998) Inhibitory Effect of Furanonaphthoquinone Derivatives on the Replication of Japanese Encephalitis Virus. Antiviral Research, 37, 37-45. [2] Inagaki, R., Ninomiya, M., Tanaka, K., Watanabe, K. and Koketsu, M. (2013) Synthesis and Cytotoxicity on Human Leukemia Cells of Furonaphthoquinones Isolated from Tabebuia Plants. Chemical & Pharmaceutical Bulletin, 61, 670-673.
http://dx.doi.org/10.1248/cpb.c13-00011 [3] Thomson, R.H. (1997) Naturally Occurring Quinones IV, Recent Advances. Blackie Academics & Professional, London, 112-308.
Diaz, F. and Medina, J.D. (1996) Furanonaphthoquinones from Tabebuia ochracea ssp. Neochrysanta. Journal of Natural Products, 59, 423-424.
Corral, J.M.D., Castro, M., Oliveira, A., Gualberto, S., Cuevas, C. and San, A.F. (2006) New Cytotoxic Furoquinones Obtained from Terpenyl-1,4-naphthoquinones and 1,4-Anthracenediones. Bioorganic & Medicinal Chemistry, 14, 7231-7240.
Kobayashi, K., Uneda, T., Kawakita, M., Morikawa, O. and Konishi, H. (1997) One-Pot Synthesis of Naphtho[2,3-b] furan-4,9-diones by Sequential Coupling/Ring Closure Reactions. Tetrahedron Letters, 38, 837-840. [4] Kobayashi, K., Shimizu, H., Sakai, A. and Suginome, H. (1993) Photoinduced Molecular Transformations. 140. New One-Step General Synthesis of Naphtho[2,3-b]furan-4,9-diones and Their 2,3-Dihydro Derivatives by the Regi-oselective [3 + 2] Photoaddition of 2-Hydroxy-1,4-naphthoquinones with Various Alkynes and Alkenes: Application of the Photoaddition to a Two-Step Synthesis of Maturinone. Journal of Organic Chemistry, 58, 4614-4618.
http://dx.doi.org/10.1021/jo00069a023
Kobayashi, K., Kanno, Y. and Suginome, H. (1993) Photoinduced Molecular Transformations. Part 141. New One-Step General Synthesis of Benzofuran-4,7-diones by the Regioselective (3 + 2) Photoaddition of 2-Hydroxy-1,4-ben-zoquinones with Various Alkenes. Journal of the Chemical Society, Perkin Transactions, 1, 1449-1452.
Lee, Y.R., Suk, J.Y. and Kim, B.S. (2000) One-Pot Construction of Medium- and Large-Sized Ring Substituted Furans. Efficient Conversion to Dibenzofurans, Coumestans, and 4-Pyrones. Organic Letters, 2, 1387-1389. [5] Hauser, F.M., Dorsch, W.A. and Mal, D. (2002) Total Synthesis of (±)-O-Methyl PD 116740. Organic Letters, 4, 2237-2239.
Mal, D., Senapati, B.K. and Pahari, P. (2006) Regioselective Synthesis of 1-Hydroxycarbazoles via Anionic [4 + 2] Cycloaddition of Furoindolones: A Short Synthesis of Murrayafoline-A. Tetrahedron Letters, 47, 1071-1075.
http://dx.doi.org/10.1016/j.tetlet.2005.12.048
Mal, D., Senapati, B.K. and Pahari, P. (2007) Anionic [4 + 2] Cycloaddition Strategy in the Regiospecific Synthesis of Carbazoles: Formal Synthesis of Ellipticine and Murrayaquinone A. Tetrahedron, 63, 3768-3781.
http://dx.doi.org/10.1016/j.tet.2007.02.060
Mal, D. and Pahari, P. (2007) Recent Advances in the Hauser Annulation. Chemical Reviews, 107, 1892-1918. [6] Mal, D., Bandhyopadhyay, M., Datta, K. and Murty, K.V.S.N. (1998) Anionic [4 + 2] Cycloaddition Strategy to Linear Furocoumarins: Synthesis of 8-Methoxypsoralen and Its Isoster. Tetrahedron, 54, 7525-7538.
http://dx.doi.org/10.1016/S0040-4020(98)00387-1 [7] Feldman, K.S. (2006) Modern Pummerer-Type Reactions. Tetrahedron, 62, 5003-5034.
http://dx.doi.org/10.1016/j.tet.2006.03.004
Padwa, A. (2004) Tandem Methodology for Heterocyclic Synthesis. Pure and Applied Chemistry, 76, 1933-1952.
Bur, S.K. and Padwa, A. (2004) The Pummerer Reaction:? Methodology and Strategy for the Synthesis of Heterocyclic Compounds. Chemical Reviews, 104, 2401-2432. [8] Padwa, A., Danca, M.D., Hardcastle, K.I. and McClure, M.S. (2003) A Short Diastereoselective Synthesis of the Putative Alkaloid Jamtine, Using a Tandem Pummerer/Mannich Cyclization Sequence. Journal of Organic Chemistry, 68, 929-941.
Hauser, F.M., Rhee, R.P. and Prasanna, S. (1980) ortho-Toluate Carbanion Chemistry: Sulfenylation and Selenation. Synthesis, 1, 72-74.
http://dx.doi.org/10.1055/s-1980-28963 [9] Murphy, P.V., O’Sullivian, T.J., Kenndy, B.D. and Geraghty, N.W. (2000) The Reactions of Diazo Compounds with Lactones. Part 2. The Reaction of Cyclic 2-Diazo-1,3-dicarbonyl Compounds with Diketene: Benzofuranformation. Journal of the Chemical Society, Perkin Transactions, 1, 2121-2126.
http://dx.doi.org/10.1039/b001394n [10] Pirrung, M.C. and Lee, Y.R. (1994) Dipolar Cycloaddition of Rhodium Carbenoids with Vinyl Esters. Total Synthesis of Pongamol and Lanceolatin B. Tetrahedron Letters, 35, 6231-6234.
http://dx.doi.org/10.1016/S0040-4039(00)73399-5 [11] Pevzner, L.M. (2001) Synthesis and Properties of (1,3-Dioxolan-2-yl)furans. Russian Journal of General Chemistry, 71, 1045-1049.
http://dx.doi.org/10.1023/A:1013149519992 [12] Parr, R.G. and Yang, W. (1989) Density Functional Theory of Atoms and Molecules. Oxford University Press, Oxford. [13] Khatuya, H. (2001) On the Bromination of Methyl 2-Methyl-3-Furoate. Tetrahedron Letters, 42, 2643-2644.
http://dx.doi.org/10.1016/S0040-4039(01)00275-1 [14] Yamamoto, T. and Sekine, Y. (1984) Condensation of Thiophenols with Aryl Halides Using Metallic Copper as a Reactant. Intermediation of Cuprous Thiophenolates. Canadian Journal of Chemistry, 62, 1544-1547.
http://dx.doi.org/10.1139/v84-263 [15] Tanikaga, R., Miyashita, K., Ono, N. and Kaji, A. (1982) A Convenient Synthesis of 2-Alkenoic Esters. Synthesis, 1982, 131-132.
http://dx.doi.org/10.1055/s-1982-29714 [16] Clayden, J., Greeves, N., Warren, S. and Wothers, P. (2001) Organic Chemistry. Oxford University Press Inc., New York, 1133.
Vegh, D., Morel, J., Decroix, B. and Zalupsky, P. (1992) A New Convenient Method for Preparation of Condensed Aromatic and Heterocyclic Thiolactones. Synthetic Communications, 22, 2057-2061.
http://dx.doi.org/10.1080/00397919208021340 [17] Curphey, T.J. (1998) Preparation of p-Toluenesulfonyl Azide. A Cautionary Note. Organic Preparations and Procedures International, 13, 112-115.
http://dx.doi.org/10.1080/00304948109356105
[1] Lin, K.I., Su, J.C., Chien, C.M., Tseng, C.H., Chen, Y.L., Chang, L.S. and Lin, S.R. (2010) Naphtho[1,2-b]furan-4,5- dione Induces Apoptosis and S-Phase Arrest of MDA-MB-231 Cells through JNK and ERK Signaling Activation. Toxicology in Vitro, 24, 61-70.
http://dx.doi.org/10.1016/j.tiv.2009.09.002
Ito, C., Katsuno, S., Kondo, Y., Tan, H.T.W. and Fu-rukawa, H. (2000) Chemical Constituents of Avicennia Alba. Isolation and Structural Elucidation of New Naphthoquinones and Their Analogues. Chemical & Pharmaceutical Bulletin, 48, 339-343.
Hirai, K., Koyama, J., Pan, J., Simamura, E., Shimada, H. and Yamori, T. (1999) Cancer Detection and Prevention, 23, 539-550.
Nagata, K., Hirai, K., Koyama, J., Wada, Y. and Tamura, T. (1998) Antimicrobial Agents and Chemotherapy, 42, 700-702.
Takegami, T., Simamura, E., Hirai, K. and Koyama, J. (1998) Inhibitory Effect of Furanonaphthoquinone Derivatives on the Replication of Japanese Encephalitis Virus. Antiviral Research, 37, 37-45. [2] Inagaki, R., Ninomiya, M., Tanaka, K., Watanabe, K. and Koketsu, M. (2013) Synthesis and Cytotoxicity on Human Leukemia Cells of Furonaphthoquinones Isolated from Tabebuia Plants. Chemical & Pharmaceutical Bulletin, 61, 670-673.
http://dx.doi.org/10.1248/cpb.c13-00011 [3] Thomson, R.H. (1997) Naturally Occurring Quinones IV, Recent Advances. Blackie Academics & Professional, London, 112-308.
Diaz, F. and Medina, J.D. (1996) Furanonaphthoquinones from Tabebuia ochracea ssp. Neochrysanta. Journal of Natural Products, 59, 423-424.
Corral, J.M.D., Castro, M., Oliveira, A., Gualberto, S., Cuevas, C. and San, A.F. (2006) New Cytotoxic Furoquinones Obtained from Terpenyl-1,4-naphthoquinones and 1,4-Anthracenediones. Bioorganic & Medicinal Chemistry, 14, 7231-7240.
Kobayashi, K., Uneda, T., Kawakita, M., Morikawa, O. and Konishi, H. (1997) One-Pot Synthesis of Naphtho[2,3-b] furan-4,9-diones by Sequential Coupling/Ring Closure Reactions. Tetrahedron Letters, 38, 837-840. [4] Kobayashi, K., Shimizu, H., Sakai, A. and Suginome, H. (1993) Photoinduced Molecular Transformations. 140. New One-Step General Synthesis of Naphtho[2,3-b]furan-4,9-diones and Their 2,3-Dihydro Derivatives by the Regi-oselective [3 + 2] Photoaddition of 2-Hydroxy-1,4-naphthoquinones with Various Alkynes and Alkenes: Application of the Photoaddition to a Two-Step Synthesis of Maturinone. Journal of Organic Chemistry, 58, 4614-4618.
http://dx.doi.org/10.1021/jo00069a023
Kobayashi, K., Kanno, Y. and Suginome, H. (1993) Photoinduced Molecular Transformations. Part 141. New One-Step General Synthesis of Benzofuran-4,7-diones by the Regioselective (3 + 2) Photoaddition of 2-Hydroxy-1,4-ben-zoquinones with Various Alkenes. Journal of the Chemical Society, Perkin Transactions, 1, 1449-1452.
Lee, Y.R., Suk, J.Y. and Kim, B.S. (2000) One-Pot Construction of Medium- and Large-Sized Ring Substituted Furans. Efficient Conversion to Dibenzofurans, Coumestans, and 4-Pyrones. Organic Letters, 2, 1387-1389. [5] Hauser, F.M., Dorsch, W.A. and Mal, D. (2002) Total Synthesis of (±)-O-Methyl PD 116740. Organic Letters, 4, 2237-2239.
Mal, D., Senapati, B.K. and Pahari, P. (2006) Regioselective Synthesis of 1-Hydroxycarbazoles via Anionic [4 + 2] Cycloaddition of Furoindolones: A Short Synthesis of Murrayafoline-A. Tetrahedron Letters, 47, 1071-1075.
http://dx.doi.org/10.1016/j.tetlet.2005.12.048
Mal, D., Senapati, B.K. and Pahari, P. (2007) Anionic [4 + 2] Cycloaddition Strategy in the Regiospecific Synthesis of Carbazoles: Formal Synthesis of Ellipticine and Murrayaquinone A. Tetrahedron, 63, 3768-3781.
http://dx.doi.org/10.1016/j.tet.2007.02.060
Mal, D. and Pahari, P. (2007) Recent Advances in the Hauser Annulation. Chemical Reviews, 107, 1892-1918. [6] Mal, D., Bandhyopadhyay, M., Datta, K. and Murty, K.V.S.N. (1998) Anionic [4 + 2] Cycloaddition Strategy to Linear Furocoumarins: Synthesis of 8-Methoxypsoralen and Its Isoster. Tetrahedron, 54, 7525-7538.
http://dx.doi.org/10.1016/S0040-4020(98)00387-1 [7] Feldman, K.S. (2006) Modern Pummerer-Type Reactions. Tetrahedron, 62, 5003-5034.
http://dx.doi.org/10.1016/j.tet.2006.03.004
Padwa, A. (2004) Tandem Methodology for Heterocyclic Synthesis. Pure and Applied Chemistry, 76, 1933-1952.
Bur, S.K. and Padwa, A. (2004) The Pummerer Reaction:? Methodology and Strategy for the Synthesis of Heterocyclic Compounds. Chemical Reviews, 104, 2401-2432. [8] Padwa, A., Danca, M.D., Hardcastle, K.I. and McClure, M.S. (2003) A Short Diastereoselective Synthesis of the Putative Alkaloid Jamtine, Using a Tandem Pummerer/Mannich Cyclization Sequence. Journal of Organic Chemistry, 68, 929-941.
Hauser, F.M., Rhee, R.P. and Prasanna, S. (1980) ortho-Toluate Carbanion Chemistry: Sulfenylation and Selenation. Synthesis, 1, 72-74.
http://dx.doi.org/10.1055/s-1980-28963 [9] Murphy, P.V., O’Sullivian, T.J., Kenndy, B.D. and Geraghty, N.W. (2000) The Reactions of Diazo Compounds with Lactones. Part 2. The Reaction of Cyclic 2-Diazo-1,3-dicarbonyl Compounds with Diketene: Benzofuranformation. Journal of the Chemical Society, Perkin Transactions, 1, 2121-2126.
http://dx.doi.org/10.1039/b001394n [10] Pirrung, M.C. and Lee, Y.R. (1994) Dipolar Cycloaddition of Rhodium Carbenoids with Vinyl Esters. Total Synthesis of Pongamol and Lanceolatin B. Tetrahedron Letters, 35, 6231-6234.
http://dx.doi.org/10.1016/S0040-4039(00)73399-5 [11] Pevzner, L.M. (2001) Synthesis and Properties of (1,3-Dioxolan-2-yl)furans. Russian Journal of General Chemistry, 71, 1045-1049.
http://dx.doi.org/10.1023/A:1013149519992 [12] Parr, R.G. and Yang, W. (1989) Density Functional Theory of Atoms and Molecules. Oxford University Press, Oxford. [13] Khatuya, H. (2001) On the Bromination of Methyl 2-Methyl-3-Furoate. Tetrahedron Letters, 42, 2643-2644.
http://dx.doi.org/10.1016/S0040-4039(01)00275-1 [14] Yamamoto, T. and Sekine, Y. (1984) Condensation of Thiophenols with Aryl Halides Using Metallic Copper as a Reactant. Intermediation of Cuprous Thiophenolates. Canadian Journal of Chemistry, 62, 1544-1547.
http://dx.doi.org/10.1139/v84-263 [15] Tanikaga, R., Miyashita, K., Ono, N. and Kaji, A. (1982) A Convenient Synthesis of 2-Alkenoic Esters. Synthesis, 1982, 131-132.
http://dx.doi.org/10.1055/s-1982-29714 [16] Clayden, J., Greeves, N., Warren, S. and Wothers, P. (2001) Organic Chemistry. Oxford University Press Inc., New York, 1133.
Vegh, D., Morel, J., Decroix, B. and Zalupsky, P. (1992) A New Convenient Method for Preparation of Condensed Aromatic and Heterocyclic Thiolactones. Synthetic Communications, 22, 2057-2061.
http://dx.doi.org/10.1080/00397919208021340 [17] Curphey, T.J. (1998) Preparation of p-Toluenesulfonyl Azide. A Cautionary Note. Organic Preparations and Procedures International, 13, 112-115.
http://dx.doi.org/10.1080/00304948109356105