Regioselective synthesis of cytotoxic 4-(1-alkynyl)-substituted 2-(5H)-furanones

Tetrahedron

Volumn 59, Issue 46, 2003, Pages 9091-9100

  Bellina, Fabio ^a   Falchi, Elisabetta ^a   Rossi, Renzo ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

2 (5H) furanones; Cytotoxicity; Palladium catalysis; Regioselectivity; Sonogashira reaction

Indexed keywords

3 BROMO 4 (1 OCTYNYL) 2(5H) FURANONE; 3 BROMO 4 (3 HYDROXY 3 METHYL 1 BUTYNYL) 2(5H) FURANONE; 3 BROMO 4 (3,3 DIMETHYL 1 BUTYNYL) 2(5H) FURANONE; 3 BROMO 4 (4 TOLYL)ETHYNYL 2(5H) FURANONE; 3 BROMO 4 PHENYLETHYNYL 2(5H) FURANONE; 3 CHLORO 4 (PHENYLETHYNYL) 2(5H) FURANONE; 3 [(2 METHOXYMETHOXY)PHENYL] 4 PHENYLETHYNYL 2(5H) FURANONE; 4 (1 HEXYNYL) 3 (4 METHOXYPHENYL) 2(5H) FURANONE; ALKYNE; ANTINEOPLASTIC AGENT; COPPER; FURANONE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; PRIORITY JOURNAL; SONOGASHIRA REACTION; STEREOCHEMISTRY; STILLE REACTION; SUZUKI REACTION;

LATEOLABRAX JAPONICUS;

EID: 0142196135     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.061     Document Type: Article

References (50)

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17. For leading references on this reaction, see: (a) Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 16:1975;4467-4470 (b) Rossi R., Carpita A., Bellina F. Org. Prep. Proced. Int. 27:1995;127-160 (c) Sonogashira K. Diederich F., Stang P.J. Metal Catalyzed Cross Coupling Reactions. 1998;Wiley, Weinheim. Chapter 5 (d) Sonogashira K. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;521-549 Pergamon, New York, (e) Kabalka G.W., Wang L., Namboodiri V., Pagni R.M. Tetrahedron Lett. 41:2000;5151-5154. (these Authors used a commercially available alumina-KF mixture as a base and performed the Sonogashira reaction in the presence of microwaves) (f) Kabalka G.W., Wang L., Pagni R.M. Tetrahedron. 57:2001;8017-8028 (g) Halbes U., Pale P. Tetrahedron Lett. 43:2002;2039-2042 (h) Langille N.F., Dakin L.A., Panek J.S. Org. Lett. 4:2002;2485-2488 (i) Erdélyi M., Gogoll A. J. Org. Chem. 66:2001;4165-4169 (j) Gallagher W.P., Maleczka R.E. Jr. Synlett. 2003;537-541 (k) Hundertmark T., Littke A.F., Buchwald S.L., Fu G.C. Org. Lett. 2:2000;1729-1731 (l) Cosford N.P.D., Tehrani L., Roppe J., Schweiger E., Smith N.D., Anderson J., Bristow L., Brodkin J., Jiang X., McDonald I., Rao S., Washburn M., Varney M.A. J. Med. Chem. 46:2003;204-206 (m) Feuerstein M., Berthiol F., Doucet H., Santelli M. Org. Biomol. Chem. 1:2003;2235-2237 (n) Nájera C., Gil-Moltó J., Karlström S., Falvello L.R. Org. Lett. 5:2003;1451-1454 (o) Beletskaya I.P., Latyshev G.V., Tsvetkov A.V., Lukashev N.V. Tetrahedron Lett. 44:2003;5011-5013.
18. For leading references on this reaction, see: (a) Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 16:1975;4467-4470 (b) Rossi R., Carpita A., Bellina F. Org. Prep. Proced. Int. 27:1995;127-160 (c) Sonogashira K. Diederich F., Stang P.J. Metal Catalyzed Cross Coupling Reactions. 1998;Wiley, Weinheim. Chapter 5 (d) Sonogashira K. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;521-549 Pergamon, New York, (e) Kabalka G.W., Wang L., Namboodiri V., Pagni R.M. Tetrahedron Lett. 41:2000;5151-5154. (these Authors used a commercially available alumina-KF mixture as a base and performed the Sonogashira reaction in the presence of microwaves) (f) Kabalka G.W., Wang L., Pagni R.M. Tetrahedron. 57:2001;8017-8028 (g) Halbes U., Pale P. Tetrahedron Lett. 43:2002;2039-2042 (h) Langille N.F., Dakin L.A., Panek J.S. Org. Lett. 4:2002;2485-2488 (i) Erdélyi M., Gogoll A. J. Org. Chem. 66:2001;4165-4169 (j) Gallagher W.P., Maleczka R.E. Jr. Synlett. 2003;537-541 (k) Hundertmark T., Littke A.F., Buchwald S.L., Fu G.C. Org. Lett. 2:2000;1729-1731 (l) Cosford N.P.D., Tehrani L., Roppe J., Schweiger E., Smith N.D., Anderson J., Bristow L., Brodkin J., Jiang X., McDonald I., Rao S., Washburn M., Varney M.A. J. Med. Chem. 46:2003;204-206 (m) Feuerstein M., Berthiol F., Doucet H., Santelli M. Org. Biomol. Chem. 1:2003;2235-2237 (n) Nájera C., Gil-Moltó J., Karlström S., Falvello L.R. Org. Lett. 5:2003;1451-1454 (o) Beletskaya I.P., Latyshev G.V., Tsvetkov A.V., Lukashev N.V. Tetrahedron Lett. 44:2003;5011-5013.
19. For leading references on this reaction, see: (a) Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 16:1975;4467-4470 (b) Rossi R., Carpita A., Bellina F. Org. Prep. Proced. Int. 27:1995;127-160 (c) Sonogashira K. Diederich F., Stang P.J. Metal Catalyzed Cross Coupling Reactions. 1998;Wiley, Weinheim. Chapter 5 (d) Sonogashira K. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;521-549 Pergamon, New York, (e) Kabalka G.W., Wang L., Namboodiri V., Pagni R.M. Tetrahedron Lett. 41:2000;5151-5154. (these Authors used a commercially available alumina-KF mixture as a base and performed the Sonogashira reaction in the presence of microwaves) (f) Kabalka G.W., Wang L., Pagni R.M. Tetrahedron. 57:2001;8017-8028 (g) Halbes U., Pale P. Tetrahedron Lett. 43:2002;2039-2042 (h) Langille N.F., Dakin L.A., Panek J.S. Org. Lett. 4:2002;2485-2488 (i) Erdélyi M., Gogoll A. J. Org. Chem. 66:2001;4165-4169 (j) Gallagher W.P., Maleczka R.E. Jr. Synlett. 2003;537-541 (k) Hundertmark T., Littke A.F., Buchwald S.L., Fu G.C. Org. Lett. 2:2000;1729-1731 (l) Cosford N.P.D., Tehrani L., Roppe J., Schweiger E., Smith N.D., Anderson J., Bristow L., Brodkin J., Jiang X., McDonald I., Rao S., Washburn M., Varney M.A. J. Med. Chem. 46:2003;204-206 (m) Feuerstein M., Berthiol F., Doucet H., Santelli M. Org. Biomol. Chem. 1:2003;2235-2237 (n) Nájera C., Gil-Moltó J., Karlström S., Falvello L.R. Org. Lett. 5:2003;1451-1454 (o) Beletskaya I.P., Latyshev G.V., Tsvetkov A.V., Lukashev N.V. Tetrahedron Lett. 44:2003;5011-5013.
20. For leading references on this reaction, see: (a) Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 16:1975;4467-4470 (b) Rossi R., Carpita A., Bellina F. Org. Prep. Proced. Int. 27:1995;127-160 (c) Sonogashira K. Diederich F., Stang P.J. Metal Catalyzed Cross Coupling Reactions. 1998;Wiley, Weinheim. Chapter 5 (d) Sonogashira K. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;521-549 Pergamon, New York, (e) Kabalka G.W., Wang L., Namboodiri V., Pagni R.M. Tetrahedron Lett. 41:2000;5151-5154. (these Authors used a commercially available alumina-KF mixture as a base and performed the Sonogashira reaction in the presence of microwaves) (f) Kabalka G.W., Wang L., Pagni R.M. Tetrahedron. 57:2001;8017-8028 (g) Halbes U., Pale P. Tetrahedron Lett. 43:2002;2039-2042 (h) Langille N.F., Dakin L.A., Panek J.S. Org. Lett. 4:2002;2485-2488 (i) Erdélyi M., Gogoll A. J. Org. Chem. 66:2001;4165-4169 (j) Gallagher W.P., Maleczka R.E. Jr. Synlett. 2003;537-541 (k) Hundertmark T., Littke A.F., Buchwald S.L., Fu G.C. Org. Lett. 2:2000;1729-1731 (l) Cosford N.P.D., Tehrani L., Roppe J., Schweiger E., Smith N.D., Anderson J., Bristow L., Brodkin J., Jiang X., McDonald I., Rao S., Washburn M., Varney M.A. J. Med. Chem. 46:2003;204-206 (m) Feuerstein M., Berthiol F., Doucet H., Santelli M. Org. Biomol. Chem. 1:2003;2235-2237 (n) Nájera C., Gil-Moltó J., Karlström S., Falvello L.R. Org. Lett. 5:2003;1451-1454 (o) Beletskaya I.P., Latyshev G.V., Tsvetkov A.V., Lukashev N.V. Tetrahedron Lett. 44:2003;5011-5013.
21. For leading references on this reaction, see: (a) Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 16:1975;4467-4470 (b) Rossi R., Carpita A., Bellina F. Org. Prep. Proced. Int. 27:1995;127-160 (c) Sonogashira K. Diederich F., Stang P.J. Metal Catalyzed Cross Coupling Reactions. 1998;Wiley, Weinheim. Chapter 5 (d) Sonogashira K. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;521-549 Pergamon, New York, (e) Kabalka G.W., Wang L., Namboodiri V., Pagni R.M. Tetrahedron Lett. 41:2000;5151-5154. (these Authors used a commercially available alumina-KF mixture as a base and performed the Sonogashira reaction in the presence of microwaves) (f) Kabalka G.W., Wang L., Pagni R.M. Tetrahedron. 57:2001;8017-8028 (g) Halbes U., Pale P. Tetrahedron Lett. 43:2002;2039-2042 (h) Langille N.F., Dakin L.A., Panek J.S. Org. Lett. 4:2002;2485-2488 (i) Erdélyi M., Gogoll A. J. Org. Chem. 66:2001;4165-4169 (j) Gallagher W.P., Maleczka R.E. Jr. Synlett. 2003;537-541 (k) Hundertmark T., Littke A.F., Buchwald S.L., Fu G.C. Org. Lett. 2:2000;1729-1731 (l) Cosford N.P.D., Tehrani L., Roppe J., Schweiger E., Smith N.D., Anderson J., Bristow L., Brodkin J., Jiang X., McDonald I., Rao S., Washburn M., Varney M.A. J. Med. Chem. 46:2003;204-206 (m) Feuerstein M., Berthiol F., Doucet H., Santelli M. Org. Biomol. Chem. 1:2003;2235-2237 (n) Nájera C., Gil-Moltó J., Karlström S., Falvello L.R. Org. Lett. 5:2003;1451-1454 (o) Beletskaya I.P., Latyshev G.V., Tsvetkov A.V., Lukashev N.V. Tetrahedron Lett. 44:2003;5011-5013.
22. For leading references on this reaction, see: (a) Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 16:1975;4467-4470 (b) Rossi R., Carpita A., Bellina F. Org. Prep. Proced. Int. 27:1995;127-160 (c) Sonogashira K. Diederich F., Stang P.J. Metal Catalyzed Cross Coupling Reactions. 1998;Wiley, Weinheim. Chapter 5 (d) Sonogashira K. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;521-549 Pergamon, New York, (e) Kabalka G.W., Wang L., Namboodiri V., Pagni R.M. Tetrahedron Lett. 41:2000;5151-5154. (these Authors used a commercially available alumina-KF mixture as a base and performed the Sonogashira reaction in the presence of microwaves) (f) Kabalka G.W., Wang L., Pagni R.M. Tetrahedron. 57:2001;8017-8028 (g) Halbes U., Pale P. Tetrahedron Lett. 43:2002;2039-2042 (h) Langille N.F., Dakin L.A., Panek J.S. Org. Lett. 4:2002;2485-2488 (i) Erdélyi M., Gogoll A. J. Org. Chem. 66:2001;4165-4169 (j) Gallagher W.P., Maleczka R.E. Jr. Synlett. 2003;537-541 (k) Hundertmark T., Littke A.F., Buchwald S.L., Fu G.C. Org. Lett. 2:2000;1729-1731 (l) Cosford N.P.D., Tehrani L., Roppe J., Schweiger E., Smith N.D., Anderson J., Bristow L., Brodkin J., Jiang X., McDonald I., Rao S., Washburn M., Varney M.A. J. Med. Chem. 46:2003;204-206 (m) Feuerstein M., Berthiol F., Doucet H., Santelli M. Org. Biomol. Chem. 1:2003;2235-2237 (n) Nájera C., Gil-Moltó J., Karlström S., Falvello L.R. Org. Lett. 5:2003;1451-1454 (o) Beletskaya I.P., Latyshev G.V., Tsvetkov A.V., Lukashev N.V. Tetrahedron Lett. 44:2003;5011-5013.
23. For leading references on this reaction, see: (a) Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 16:1975;4467-4470 (b) Rossi R., Carpita A., Bellina F. Org. Prep. Proced. Int. 27:1995;127-160 (c) Sonogashira K. Diederich F., Stang P.J. Metal Catalyzed Cross Coupling Reactions. 1998;Wiley, Weinheim. Chapter 5 (d) Sonogashira K. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;521-549 Pergamon, New York, (e) Kabalka G.W., Wang L., Namboodiri V., Pagni R.M. Tetrahedron Lett. 41:2000;5151-5154. (these Authors used a commercially available alumina-KF mixture as a base and performed the Sonogashira reaction in the presence of microwaves) (f) Kabalka G.W., Wang L., Pagni R.M. Tetrahedron. 57:2001;8017-8028 (g) Halbes U., Pale P. Tetrahedron Lett. 43:2002;2039-2042 (h) Langille N.F., Dakin L.A., Panek J.S. Org. Lett. 4:2002;2485-2488 (i) Erdélyi M., Gogoll A. J. Org. Chem. 66:2001;4165-4169 (j) Gallagher W.P., Maleczka R.E. Jr. Synlett. 2003;537-541 (k) Hundertmark T., Littke A.F., Buchwald S.L., Fu G.C. Org. Lett. 2:2000;1729-1731 (l) Cosford N.P.D., Tehrani L., Roppe J., Schweiger E., Smith N.D., Anderson J., Bristow L., Brodkin J., Jiang X., McDonald I., Rao S., Washburn M., Varney M.A. J. Med. Chem. 46:2003;204-206 (m) Feuerstein M., Berthiol F., Doucet H., Santelli M. Org. Biomol. Chem. 1:2003;2235-2237 (n) Nájera C., Gil-Moltó J., Karlström S., Falvello L.R. Org. Lett. 5:2003;1451-1454 (o) Beletskaya I.P., Latyshev G.V., Tsvetkov A.V., Lukashev N.V. Tetrahedron Lett. 44:2003;5011-5013.
24. For leading references on this reaction, see: (a) Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 16:1975;4467-4470 (b) Rossi R., Carpita A., Bellina F. Org. Prep. Proced. Int. 27:1995;127-160 (c) Sonogashira K. Diederich F., Stang P.J. Metal Catalyzed Cross Coupling Reactions. 1998;Wiley, Weinheim. Chapter 5 (d) Sonogashira K. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;521-549 Pergamon, New York, (e) Kabalka G.W., Wang L., Namboodiri V., Pagni R.M. Tetrahedron Lett. 41:2000;5151-5154. (these Authors used a commercially available alumina-KF mixture as a base and performed the Sonogashira reaction in the presence of microwaves) (f) Kabalka G.W., Wang L., Pagni R.M. Tetrahedron. 57:2001;8017-8028 (g) Halbes U., Pale P. Tetrahedron Lett. 43:2002;2039-2042 (h) Langille N.F., Dakin L.A., Panek J.S. Org. Lett. 4:2002;2485-2488 (i) Erdélyi M., Gogoll A. J. Org. Chem. 66:2001;4165-4169 (j) Gallagher W.P., Maleczka R.E. Jr. Synlett. 2003;537-541 (k) Hundertmark T., Littke A.F., Buchwald S.L., Fu G.C. Org. Lett. 2:2000;1729-1731 (l) Cosford N.P.D., Tehrani L., Roppe J., Schweiger E., Smith N.D., Anderson J., Bristow L., Brodkin J., Jiang X., McDonald I., Rao S., Washburn M., Varney M.A. J. Med. Chem. 46:2003;204-206 (m) Feuerstein M., Berthiol F., Doucet H., Santelli M. Org. Biomol. Chem. 1:2003;2235-2237 (n) Nájera C., Gil-Moltó J., Karlström S., Falvello L.R. Org. Lett. 5:2003;1451-1454 (o) Beletskaya I.P., Latyshev G.V., Tsvetkov A.V., Lukashev N.V. Tetrahedron Lett. 44:2003;5011-5013.
25. For leading references on this reaction, see: (a) Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 16:1975;4467-4470 (b) Rossi R., Carpita A., Bellina F. Org. Prep. Proced. Int. 27:1995;127-160 (c) Sonogashira K. Diederich F., Stang P.J. Metal Catalyzed Cross Coupling Reactions. 1998;Wiley, Weinheim. Chapter 5 (d) Sonogashira K. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;521-549 Pergamon, New York, (e) Kabalka G.W., Wang L., Namboodiri V., Pagni R.M. Tetrahedron Lett. 41:2000;5151-5154. (these Authors used a commercially available alumina-KF mixture as a base and performed the Sonogashira reaction in the presence of microwaves) (f) Kabalka G.W., Wang L., Pagni R.M. Tetrahedron. 57:2001;8017-8028 (g) Halbes U., Pale P. Tetrahedron Lett. 43:2002;2039-2042 (h) Langille N.F., Dakin L.A., Panek J.S. Org. Lett. 4:2002;2485-2488 (i) Erdélyi M., Gogoll A. J. Org. Chem. 66:2001;4165-4169 (j) Gallagher W.P., Maleczka R.E. Jr. Synlett. 2003;537-541 (k) Hundertmark T., Littke A.F., Buchwald S.L., Fu G.C. Org. Lett. 2:2000;1729-1731 (l) Cosford N.P.D., Tehrani L., Roppe J., Schweiger E., Smith N.D., Anderson J., Bristow L., Brodkin J., Jiang X., McDonald I., Rao S., Washburn M., Varney M.A. J. Med. Chem. 46:2003;204-206 (m) Feuerstein M., Berthiol F., Doucet H., Santelli M. Org. Biomol. Chem. 1:2003;2235-2237 (n) Nájera C., Gil-Moltó J., Karlström S., Falvello L.R. Org. Lett. 5:2003;1451-1454 (o) Beletskaya I.P., Latyshev G.V., Tsvetkov A.V., Lukashev N.V. Tetrahedron Lett. 44:2003;5011-5013.
26. For leading references on this reaction, see: (a) Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 16:1975;4467-4470 (b) Rossi R., Carpita A., Bellina F. Org. Prep. Proced. Int. 27:1995;127-160 (c) Sonogashira K. Diederich F., Stang P.J. Metal Catalyzed Cross Coupling Reactions. 1998;Wiley, Weinheim. Chapter 5 (d) Sonogashira K. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;521-549 Pergamon, New York, (e) Kabalka G.W., Wang L., Namboodiri V., Pagni R.M. Tetrahedron Lett. 41:2000;5151-5154. (these Authors used a commercially available alumina-KF mixture as a base and performed the Sonogashira reaction in the presence of microwaves) (f) Kabalka G.W., Wang L., Pagni R.M. Tetrahedron. 57:2001;8017-8028 (g) Halbes U., Pale P. Tetrahedron Lett. 43:2002;2039-2042 (h) Langille N.F., Dakin L.A., Panek J.S. Org. Lett. 4:2002;2485-2488 (i) Erdélyi M., Gogoll A. J. Org. Chem. 66:2001;4165-4169 (j) Gallagher W.P., Maleczka R.E. Jr. Synlett. 2003;537-541 (k) Hundertmark T., Littke A.F., Buchwald S.L., Fu G.C. Org. Lett. 2:2000;1729-1731 (l) Cosford N.P.D., Tehrani L., Roppe J., Schweiger E., Smith N.D., Anderson J., Bristow L., Brodkin J., Jiang X., McDonald I., Rao S., Washburn M., Varney M.A. J. Med. Chem. 46:2003;204-206 (m) Feuerstein M., Berthiol F., Doucet H., Santelli M. Org. Biomol. Chem. 1:2003;2235-2237 (n) Nájera C., Gil-Moltó J., Karlström S., Falvello L.R. Org. Lett. 5:2003;1451-1454 (o) Beletskaya I.P., Latyshev G.V., Tsvetkov A.V., Lukashev N.V. Tetrahedron Lett. 44:2003;5011-5013.
27. For leading references on this reaction, see: (a) Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 16:1975;4467-4470 (b) Rossi R., Carpita A., Bellina F. Org. Prep. Proced. Int. 27:1995;127-160 (c) Sonogashira K. Diederich F., Stang P.J. Metal Catalyzed Cross Coupling Reactions. 1998;Wiley, Weinheim. Chapter 5 (d) Sonogashira K. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;521-549 Pergamon, New York, (e) Kabalka G.W., Wang L., Namboodiri V., Pagni R.M. Tetrahedron Lett. 41:2000;5151-5154. (these Authors used a commercially available alumina-KF mixture as a base and performed the Sonogashira reaction in the presence of microwaves) (f) Kabalka G.W., Wang L., Pagni R.M. Tetrahedron. 57:2001;8017-8028 (g) Halbes U., Pale P. Tetrahedron Lett. 43:2002;2039-2042 (h) Langille N.F., Dakin L.A., Panek J.S. Org. Lett. 4:2002;2485-2488 (i) Erdélyi M., Gogoll A. J. Org. Chem. 66:2001;4165-4169 (j) Gallagher W.P., Maleczka R.E. Jr. Synlett. 2003;537-541 (k) Hundertmark T., Littke A.F., Buchwald S.L., Fu G.C. Org. Lett. 2:2000;1729-1731 (l) Cosford N.P.D., Tehrani L., Roppe J., Schweiger E., Smith N.D., Anderson J., Bristow L., Brodkin J., Jiang X., McDonald I., Rao S., Washburn M., Varney M.A. J. Med. Chem. 46:2003;204-206 (m) Feuerstein M., Berthiol F., Doucet H., Santelli M. Org. Biomol. Chem. 1:2003;2235-2237 (n) Nájera C., Gil-Moltó J., Karlström S., Falvello L.R. Org. Lett. 5:2003;1451-1454 (o) Beletskaya I.P., Latyshev G.V., Tsvetkov A.V., Lukashev N.V. Tetrahedron Lett. 44:2003;5011-5013.
28. For leading references on this reaction, see: (a) Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 16:1975;4467-4470 (b) Rossi R., Carpita A., Bellina F. Org. Prep. Proced. Int. 27:1995;127-160 (c) Sonogashira K. Diederich F., Stang P.J. Metal Catalyzed Cross Coupling Reactions. 1998;Wiley, Weinheim. Chapter 5 (d) Sonogashira K. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;521-549 Pergamon, New York, (e) Kabalka G.W., Wang L., Namboodiri V., Pagni R.M. Tetrahedron Lett. 41:2000;5151-5154. (these Authors used a commercially available alumina-KF mixture as a base and performed the Sonogashira reaction in the presence of microwaves) (f) Kabalka G.W., Wang L., Pagni R.M. Tetrahedron. 57:2001;8017-8028 (g) Halbes U., Pale P. Tetrahedron Lett. 43:2002;2039-2042 (h) Langille N.F., Dakin L.A., Panek J.S. Org. Lett. 4:2002;2485-2488 (i) Erdélyi M., Gogoll A. J. Org. Chem. 66:2001;4165-4169 (j) Gallagher W.P., Maleczka R.E. Jr. Synlett. 2003;537-541 (k) Hundertmark T., Littke A.F., Buchwald S.L., Fu G.C. Org. Lett. 2:2000;1729-1731 (l) Cosford N.P.D., Tehrani L., Roppe J., Schweiger E., Smith N.D., Anderson J., Bristow L., Brodkin J., Jiang X., McDonald I., Rao S., Washburn M., Varney M.A. J. Med. Chem. 46:2003;204-206 (m) Feuerstein M., Berthiol F., Doucet H., Santelli M. Org. Biomol. Chem. 1:2003;2235-2237 (n) Nájera C., Gil-Moltó J., Karlström S., Falvello L.R. Org. Lett. 5:2003;1451-1454 (o) Beletskaya I.P., Latyshev G.V., Tsvetkov A.V., Lukashev N.V. Tetrahedron Lett. 44:2003;5011-5013.
29. For leading references on this reaction, see: (a) Sonogashira K., Tohda Y., Hagihara N. Tetrahedron Lett. 16:1975;4467-4470 (b) Rossi R., Carpita A., Bellina F. Org. Prep. Proced. Int. 27:1995;127-160 (c) Sonogashira K. Diederich F., Stang P.J. Metal Catalyzed Cross Coupling Reactions. 1998;Wiley, Weinheim. Chapter 5 (d) Sonogashira K. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;521-549 Pergamon, New York, (e) Kabalka G.W., Wang L., Namboodiri V., Pagni R.M. Tetrahedron Lett. 41:2000;5151-5154. (these Authors used a commercially available alumina-KF mixture as a base and performed the Sonogashira reaction in the presence of microwaves) (f) Kabalka G.W., Wang L., Pagni R.M. Tetrahedron. 57:2001;8017-8028 (g) Halbes U., Pale P. Tetrahedron Lett. 43:2002;2039-2042 (h) Langille N.F., Dakin L.A., Panek J.S. Org. Lett. 4:2002;2485-2488 (i) Erdélyi M., Gogoll A. J. Org. Chem. 66:2001;4165-4169 (j) Gallagher W.P., Maleczka R.E. Jr. Synlett. 2003;537-541 (k) Hundertmark T., Littke A.F., Buchwald S.L., Fu G.C. Org. Lett. 2:2000;1729-1731 (l) Cosford N.P.D., Tehrani L., Roppe J., Schweiger E., Smith N.D., Anderson J., Bristow L., Brodkin J., Jiang X., McDonald I., Rao S., Washburn M., Varney M.A. J. Med. Chem. 46:2003;204-206 (m) Feuerstein M., Berthiol F., Doucet H., Santelli M. Org. Biomol. Chem. 1:2003;2235-2237 (n) Nájera C., Gil-Moltó J., Karlström S., Falvello L.R. Org. Lett. 5:2003;1451-1454 (o) Beletskaya I.P., Latyshev G.V., Tsvetkov A.V., Lukashev N.V. Tetrahedron Lett. 44:2003;5011-5013.
30. For leading references on the use of the phase-transfer methodology in Pd-catalyzed carbon-carbon bond forming reactions, see: (a) Rossi R., Carpita A., Quirici M.G., Gaudenzi M.L. Tetrahedron. 38:1982;631-637 (b) Jeffery T., Galland J.-C. Tetrahedron Lett. 35:1994;4103-4106 (c) Jeffery T. Tetrahedron Lett. 35:1994;3051-3054 (d) Nakoi M., Kanayama T., Okino T., Takemoto Y. Org. Lett. 3:2001;3329-3332 (e) Chow H.-F., Wan C.-W., Lows K.-H., Yeung Y.-Y. J. Org. Chem. 66:2001;1910-1913 (f) Wang J.-X., Liu Z., Hu Y., Wei B., Bai L. Synth. Commun. 32:2002;1607-1614 (g) Zhang J., Blazecka P.G., Belmont D., Davidson J.G. Org. Lett. 4:2002;4559-4561.
31. For leading references on the use of the phase-transfer methodology in Pd-catalyzed carbon-carbon bond forming reactions, see: (a) Rossi R., Carpita A., Quirici M.G., Gaudenzi M.L. Tetrahedron. 38:1982;631-637 (b) Jeffery T., Galland J.-C. Tetrahedron Lett. 35:1994;4103-4106 (c) Jeffery T. Tetrahedron Lett. 35:1994;3051-3054 (d) Nakoi M., Kanayama T., Okino T., Takemoto Y. Org. Lett. 3:2001;3329-3332 (e) Chow H.-F., Wan C.-W., Lows K.-H., Yeung Y.-Y. J. Org. Chem. 66:2001;1910-1913 (f) Wang J.-X., Liu Z., Hu Y., Wei B., Bai L. Synth. Commun. 32:2002;1607-1614 (g) Zhang J., Blazecka P.G., Belmont D., Davidson J.G. Org. Lett. 4:2002;4559-4561.
32. For leading references on the use of the phase-transfer methodology in Pd-catalyzed carbon-carbon bond forming reactions, see: (a) Rossi R., Carpita A., Quirici M.G., Gaudenzi M.L. Tetrahedron. 38:1982;631-637 (b) Jeffery T., Galland J.-C. Tetrahedron Lett. 35:1994;4103-4106 (c) Jeffery T. Tetrahedron Lett. 35:1994;3051-3054 (d) Nakoi M., Kanayama T., Okino T., Takemoto Y. Org. Lett. 3:2001;3329-3332 (e) Chow H.-F., Wan C.-W., Lows K.-H., Yeung Y.-Y. J. Org. Chem. 66:2001;1910-1913 (f) Wang J.-X., Liu Z., Hu Y., Wei B., Bai L. Synth. Commun. 32:2002;1607-1614 (g) Zhang J., Blazecka P.G., Belmont D., Davidson J.G. Org. Lett. 4:2002;4559-4561.
33. For leading references on the use of the phase-transfer methodology in Pd-catalyzed carbon-carbon bond forming reactions, see: (a) Rossi R., Carpita A., Quirici M.G., Gaudenzi M.L. Tetrahedron. 38:1982;631-637 (b) Jeffery T., Galland J.-C. Tetrahedron Lett. 35:1994;4103-4106 (c) Jeffery T. Tetrahedron Lett. 35:1994;3051-3054 (d) Nakoi M., Kanayama T., Okino T., Takemoto Y. Org. Lett. 3:2001;3329-3332 (e) Chow H.-F., Wan C.-W., Lows K.-H., Yeung Y.-Y. J. Org. Chem. 66:2001;1910-1913 (f) Wang J.-X., Liu Z., Hu Y., Wei B., Bai L. Synth. Commun. 32:2002;1607-1614 (g) Zhang J., Blazecka P.G., Belmont D., Davidson J.G. Org. Lett. 4:2002;4559-4561.
34. For leading references on the use of the phase-transfer methodology in Pd-catalyzed carbon-carbon bond forming reactions, see: (a) Rossi R., Carpita A., Quirici M.G., Gaudenzi M.L. Tetrahedron. 38:1982;631-637 (b) Jeffery T., Galland J.-C. Tetrahedron Lett. 35:1994;4103-4106 (c) Jeffery T. Tetrahedron Lett. 35:1994;3051-3054 (d) Nakoi M., Kanayama T., Okino T., Takemoto Y. Org. Lett. 3:2001;3329-3332 (e) Chow H.-F., Wan C.-W., Lows K.-H., Yeung Y.-Y. J. Org. Chem. 66:2001;1910-1913 (f) Wang J.-X., Liu Z., Hu Y., Wei B., Bai L. Synth. Commun. 32:2002;1607-1614 (g) Zhang J., Blazecka P.G., Belmont D., Davidson J.G. Org. Lett. 4:2002;4559-4561.
35. For leading references on the use of the phase-transfer methodology in Pd-catalyzed carbon-carbon bond forming reactions, see: (a) Rossi R., Carpita A., Quirici M.G., Gaudenzi M.L. Tetrahedron. 38:1982;631-637 (b) Jeffery T., Galland J.-C. Tetrahedron Lett. 35:1994;4103-4106 (c) Jeffery T. Tetrahedron Lett. 35:1994;3051-3054 (d) Nakoi M., Kanayama T., Okino T., Takemoto Y. Org. Lett. 3:2001;3329-3332 (e) Chow H.-F., Wan C.-W., Lows K.-H., Yeung Y.-Y. J. Org. Chem. 66:2001;1910-1913 (f) Wang J.-X., Liu Z., Hu Y., Wei B., Bai L. Synth. Commun. 32:2002;1607-1614 (g) Zhang J., Blazecka P.G., Belmont D., Davidson J.G. Org. Lett. 4:2002;4559-4561.
36. For leading references on the use of the phase-transfer methodology in Pd-catalyzed carbon-carbon bond forming reactions, see: (a) Rossi R., Carpita A., Quirici M.G., Gaudenzi M.L. Tetrahedron. 38:1982;631-637 (b) Jeffery T., Galland J.-C. Tetrahedron Lett. 35:1994;4103-4106 (c) Jeffery T. Tetrahedron Lett. 35:1994;3051-3054 (d) Nakoi M., Kanayama T., Okino T., Takemoto Y. Org. Lett. 3:2001;3329-3332 (e) Chow H.-F., Wan C.-W., Lows K.-H., Yeung Y.-Y. J. Org. Chem. 66:2001;1910-1913 (f) Wang J.-X., Liu Z., Hu Y., Wei B., Bai L. Synth. Commun. 32:2002;1607-1614 (g) Zhang J., Blazecka P.G., Belmont D., Davidson J.G. Org. Lett. 4:2002;4559-4561.
37. For general reviews on the Stille cross-coupling reaction, see: (a) Stille J.K. Angew. Chem., Int. Ed. Engl. 25:1986;5087-5524 (b) Farina V., Krishnamurthy V., Scott W.J. Org. React. 50:1997;1-652 (c) Mitchell T.N. Diederich F., Stang P.J. Metal Catalyzed Cross-coupling Reactions. 1998;Wiley, Weinheim. Chapter 4.
38. For general reviews on the Stille cross-coupling reaction, see: (a) Stille J.K. Angew. Chem., Int. Ed. Engl. 25:1986;5087-5524 (b) Farina V., Krishnamurthy V., Scott W.J. Org. React. 50:1997;1-652 (c) Mitchell T.N. Diederich F., Stang P.J. Metal Catalyzed Cross-coupling Reactions. 1998;Wiley, Weinheim. Chapter 4.
39. For general reviews on the Stille cross-coupling reaction, see: (a) Stille J.K. Angew. Chem., Int. Ed. Engl. 25:1986;5087-5524 (b) Farina V., Krishnamurthy V., Scott W.J. Org. React. 50:1997;1-652 (c) Mitchell T.N. Diederich F., Stang P.J. Metal Catalyzed Cross-coupling Reactions. 1998;Wiley, Weinheim. Chapter 4.
40. For reviews on the Suzuki cross-coupling reaction, see: (a) Miyaura N., Suzuki A. Chem. Rev. 95:1995;2457-2483 (b) Suzuki A. Diederich F., Stang P.J. Metal Catalyzed Cross-coupling Reactions. 1998;Wiley, Weinheim. Chapter 2 (c) Stanforth S.P. Tetrahedron. 54:1998;263-303 (d) Suzuki A. J. Organomet. Chem. 576:1999;147-168.
41. For reviews on the Suzuki cross-coupling reaction, see: (a) Miyaura N., Suzuki A. Chem. Rev. 95:1995;2457-2483 (b) Suzuki A. Diederich F., Stang P.J. Metal Catalyzed Cross-coupling Reactions. 1998;Wiley, Weinheim. Chapter 2 (c) Stanforth S.P. Tetrahedron. 54:1998;263-303 (d) Suzuki A. J. Organomet. Chem. 576:1999;147-168.
42. For reviews on the Suzuki cross-coupling reaction, see: (a) Miyaura N., Suzuki A. Chem. Rev. 95:1995;2457-2483 (b) Suzuki A. Diederich F., Stang P.J. Metal Catalyzed Cross-coupling Reactions. 1998;Wiley, Weinheim. Chapter 2 (c) Stanforth S.P. Tetrahedron. 54:1998;263-303 (d) Suzuki A. J. Organomet. Chem. 576:1999;147-168.
43. For reviews on the Suzuki cross-coupling reaction, see: (a) Miyaura N., Suzuki A. Chem. Rev. 95:1995;2457-2483 (b) Suzuki A. Diederich F., Stang P.J. Metal Catalyzed Cross-coupling Reactions. 1998;Wiley, Weinheim. Chapter 2 (c) Stanforth S.P. Tetrahedron. 54:1998;263-303 (d) Suzuki A. J. Organomet. Chem. 576:1999;147-168.
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