Pd0-catalyzed coupling cyclization reaction of aryl or 1-alkenyl halides with 1,2-allenyl ketones: Scope and mechanism. An efficient assembly of 2,3,4-, 2,3,5-tri- and 2,3,4,5-tetrasubstituted furans

Chemistry - A European Journal

Volumn 9, Issue 11, 2003, Pages 2447-2456

  Ma, Shengming ^a   Zhang, Junliang ^a   Lu, Lianghua ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Allenes; C C coupling; Cyclization; Ketones; Palladium

Indexed keywords

CATALYSIS; FURAN RESINS; PALLADIUM; SUBSTITUTION REACTIONS;

CYCLIZATION REACTIONS;

KETONES;

1 (4' METHYLPHENYL) 2 BUTYLNONA 2,3 DIEN 1 ONE; 1 (4' TRIFLUOROMETHYLPHENYL) 1 BUTYLNONA 2,3 DIEN 1 ONE; 1,2 ALLENYL KETONE; 2,2 DIMETHYLTRIDECA 4,5 DIEN 3 ONE; ALKENYL GROUP; CARBONYL DERIVATIVE; FURAN DERIVATIVE; HALIDE; KETONE DERIVATIVE; OXYGEN DERIVATIVE; PALLADIUM COMPLEX; UNCLASSIFIED DRUG; ALKENE; HALOGENATED HYDROCARBON; KETONE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; CHEMISTRY;

ALKENES; CATALYSIS; CYCLIZATION; FURANS; HYDROCARBONS, HALOGENATED; KETONES; PALLADIUM;

EID: 0037662653     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200204664     Document Type: Article

References (80)

1. a) M. V. Sargent, F. M. Dean, Comprehensive Heterocyclic Chemistry, Vol. 4 (Eds.: A. R. Katrizky, C. W. Rees), Pergamon Press, New York, 1984, pp. 599-656; D. M. X. Donnelly, M. J. Meegan, Comprehensive Heterocyclic Chemistry, Vol. 4 (Eds.: A. R. Katrizky, C. W. Rees), Pergamon Press, New York, 1984, pp. 657-712;
2. a) M. V. Sargent, F. M. Dean, Comprehensive Heterocyclic Chemistry, Vol. 4 (Eds.: A. R. Katrizky, C. W. Rees), Pergamon Press, New York, 1984, pp. 599-656; D. M. X. Donnelly, M. J. Meegan, Comprehensive Heterocyclic Chemistry, Vol. 4 (Eds.: A. R. Katrizky, C. W. Rees), Pergamon Press, New York, 1984, pp. 657-712;
3. b) Natural Products Chemistry (Ed.: K. Nakanishi), Kodansha, Toyko, 1974, pp. 392-403
4. c) M. Shipman, Contemp. Org. Synth. 1995, 2, 1-17.
5. G. Vernin, G. Vernin, Chemistry of Heterocyclic Compounds in Flavoours and Aromas (Ed.: G. Vernin.), Ellis Horwood, Chichester, 1982, pp. 74-85; G. Vernin, C. Párkányi, Chemistry of Heterocyclic Compounds in Flavoours and Aromas (Ed.: G. Vernin.), Ellis Horwood, Chichester, 1982, pp. 161-165.
6. G. Vernin, G. Vernin, Chemistry of Heterocyclic Compounds in Flavoours and Aromas (Ed.: G. Vernin.), Ellis Horwood, Chichester, 1982, pp. 74-85; G. Vernin, C. Párkányi, Chemistry of Heterocyclic Compounds in Flavoours and Aromas (Ed.: G. Vernin.), Ellis Horwood, Chichester, 1982, pp. 161-165.
7. B. H. Lipshutz, Chem. Rev. 1986, 86, 795-819.
8. For recent reviews, see: a) X. Hou, H. Y. Cheung, T. Y. Hon, P. L. Kwan, T. H. Lo, S. Y. Tong, H. N. C. Wong Tetrahedron 1998, 54, 1955-2020;
9. b) B. A. Keay, Chem. Soc. Rev. 1999, 28, 209-215.
10. For the synthesis of 2,3,4-trisubstituted furans, see: a) K. Takai, M. Tezuka, Y. Kataoka, K. Utimoto, J. Org. Chem. 1990, 55, 5310-5312; b) Y. Kataoka, M. Tezuka, K. Takai, K. Utimoto, Tetrahedron 1992, 48, 3495-3502; c) N. Greeves, J. S. Torode, Synthesis 1993, 1109-1112; d) M. C. Pirrung, Y. R. Lee, Tetrahedron Lett. 1994, 35, 6231-6234.
11. For the synthesis of 2,3,4-trisubstituted furans, see: a) K. Takai, M. Tezuka, Y. Kataoka, K. Utimoto, J. Org. Chem. 1990, 55, 5310-5312; b) Y. Kataoka, M. Tezuka, K. Takai, K. Utimoto, Tetrahedron 1992, 48, 3495-3502; c) N. Greeves, J. S. Torode, Synthesis 1993, 1109-1112; d) M. C. Pirrung, Y. R. Lee, Tetrahedron Lett. 1994, 35, 6231-6234.
12. For the synthesis of 2,3,4-trisubstituted furans, see: a) K. Takai, M. Tezuka, Y. Kataoka, K. Utimoto, J. Org. Chem. 1990, 55, 5310-5312; b) Y. Kataoka, M. Tezuka, K. Takai, K. Utimoto, Tetrahedron 1992, 48, 3495-3502; c) N. Greeves, J. S. Torode, Synthesis 1993, 1109-1112; d) M. C. Pirrung, Y. R. Lee, Tetrahedron Lett. 1994, 35, 6231-6234.
13. For the synthesis of 2,3,4-trisubstituted furans, see: a) K. Takai, M. Tezuka, Y. Kataoka, K. Utimoto, J. Org. Chem. 1990, 55, 5310-5312; b) Y. Kataoka, M. Tezuka, K. Takai, K. Utimoto, Tetrahedron 1992, 48, 3495-3502; c) N. Greeves, J. S. Torode, Synthesis 1993, 1109-1112; d) M. C. Pirrung, Y. R. Lee, Tetrahedron Lett. 1994, 35, 6231-6234.
14. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
15. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
16. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
17. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
18. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
19. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
20. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
21. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
22. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
23. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
24. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
25. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
26. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
27. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
28. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
29. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
30. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
31. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
32. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
33. For the synthesis of 2,3,5-trisubstituted furans, see: a) H. Sheng, S. Lin, Y. Huang, Synthesis 1987, 1022-1023; b) H.M.L. Davies, K. R. Romines, Tetrahedron 1988, 44, 3343-3348; c) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816-5819; d) A. Arcadi, S. Cacchi, R. C. Larock, F. Marinelli, Tetrahedron Lett. 1993, 34, 2813-2816; e) M. Tiecco, L. Testaferri, M. Tingoli, F. Marini, Synlett 1994, 373-374; f) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968; g) B. Seiller, C. Bruneau, P. H. Dixneuf, Tetrahedron 1995, 51, 13089-13102; h) D. M. Sammond, T. Sammakia, Tetrahedron Lett. 1996, 37, 6065-6068; i) A. Arcadi, E. Rossi, Tetrahedron Lett. 1996, 37, 6811-6814; j) S. P. Bew, D. W. Knight, Chem. Commun. 1996, 1007-1008; k) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1997, 62, 4313-4320; l) A. Arcadi, E. Rossi, Tetrahedron 1998, 54, 15253-15272; m) C. M. Marson, S. Harper, J. Org. Chem. 1998, 63, 9223-9231; n) C. D. Brown, J. M. Chong, L. Shen, Tetrahedron 1999, 55, 14233-14242; o) F. T. Luo, A. C. Bajji, A. Jeevanandam, J. Org. Chem. 1999, 64, 1738-1740; p) J. A. Marshall, D. Zou, Tetrahedron Lett. 2000, 41, 1347-1350; q) F. Qing, W. Gao, J. Ying, J. Org. Chem. 2000, 65, 2003-2006; r) A. Arcadi, G. Cerichelli, M. Chiarini, S. D. Giuseppe, F. Marinelli, Tetrahedron Lett. 2000, 41, 9195-9198; s) J. M. Aurrecoechea, E. Pérez, M. Solay, J. Org. Chem. 2001, 66, 564-569; t) A. Jeevanandam, K. Narkunan, Y. C. Ling, J. Org. Chem. 2001, 66, 6014-6020.
34. For the synthesis of 2,3,4,5-tetrasubstituted furans, see: a) I. Minami, M. Yuhara, J. Tsuji, Tetrahedron Lett. 1987, 28, 629-632; b) J. M. Aurrecoechea, E. Pérez, Tetrahedron Lett. 2001, 42, 3839-3841; c) J. Okauchi, T. Tanaka, T. Minami, J. Org. Chem. 2001, 66, 3924-3929.
35. For the synthesis of 2,3,4,5-tetrasubstituted furans, see: a) I. Minami, M. Yuhara, J. Tsuji, Tetrahedron Lett. 1987, 28, 629-632; b) J. M. Aurrecoechea, E. Pérez, Tetrahedron Lett. 2001, 42, 3839-3841; c) J. Okauchi, T. Tanaka, T. Minami, J. Org. Chem. 2001, 66, 3924-3929.
36. For the synthesis of 2,3,4,5-tetrasubstituted furans, see: a) I. Minami, M. Yuhara, J. Tsuji, Tetrahedron Lett. 1987, 28, 629-632; b) J. M. Aurrecoechea, E. Pérez, Tetrahedron Lett. 2001, 42, 3839-3841; c) J. Okauchi, T. Tanaka, T. Minami, J. Org. Chem. 2001, 66, 3924-3929.
37. For synthesis of 2,3,4- and 2,3,5-trisubstituted furans, see: a) J. A. Marshall, W. J. DuBay, J. Org. Chem. 1993, 58, 3435-3443; b) B. Gabriele, G. Salerno, E. Lauria, J. Org. Chem. 1999, 64, 7687-7692; c) B. Gabriele, G. Salerno, F. D. Pascali, M. Costa, G. P. Chiusoli, J. Org. Chem. 1999, 64, 7693-7699.
38. For synthesis of 2,3,4- and 2,3,5-trisubstituted furans, see: a) J. A. Marshall, W. J. DuBay, J. Org. Chem. 1993, 58, 3435-3443; b) B. Gabriele, G. Salerno, E. Lauria, J. Org. Chem. 1999, 64, 7687-7692; c) B. Gabriele, G. Salerno, F. D. Pascali, M. Costa, G. P. Chiusoli, J. Org. Chem. 1999, 64, 7693-7699.
39. For synthesis of 2,3,4- and 2,3,5-trisubstituted furans, see: a) J. A. Marshall, W. J. DuBay, J. Org. Chem. 1993, 58, 3435-3443; b) B. Gabriele, G. Salerno, E. Lauria, J. Org. Chem. 1999, 64, 7687-7692; c) B. Gabriele, G. Salerno, F. D. Pascali, M. Costa, G. P. Chiusoli, J. Org. Chem. 1999, 64, 7693-7699.
40. For the synthesis of 2,3,4-trisubstituted and 2,3,4,5-tetrasubstituted furans, see: a) I. Minami, M. Yuhara, H. Watanabe, J. Tsuji, J. Organomet. Chem. 1987, 334, 225-242; b) P. Forgione, P. D. Wilson, A. G. Fallis, Tetrahedron Lett. 2000, 41, 17-20.
41. For the synthesis of 2,3,4-trisubstituted and 2,3,4,5-tetrasubstituted furans, see: a) I. Minami, M. Yuhara, H. Watanabe, J. Tsuji, J. Organomet. Chem. 1987, 334, 225-242; b) P. Forgione, P. D. Wilson, A. G. Fallis, Tetrahedron Lett. 2000, 41, 17-20.
42. For the synthesis of 2,3,5-trisubstituted and 2,3,4,5-tetrasubstituted furans, see: a) R. L. Danheiser, E. J. Stone, H. Koyama, D. S. Yamashita, C. A. Klade, J. Am. Chem. Soc. 1989, 111, 4407-4413; b) S. Cacchi, G. Fabrizi, L. Moro, J. Org. Chem. 1997, 62, 5327-5332; c) D. I. MaGee, J. D. Leach, T. C. Mallais, Tetrahedron Lett. 1997, 38, 1289-1292; d) D. I. MaGee, J. D. Leach, Tetrahedron Lett. 1997, 38, 8129-8132; e) D. I. MaGee, J. D. Leach, S. Setiadji, Tetrahedron 1999, 55, 2847-2856; f) F. Stauffer, R. Neier, Org. Lett. 2000, 2, 3535-3537.
43. For the synthesis of 2,3,5-trisubstituted and 2,3,4,5-tetrasubstituted furans, see: a) R. L. Danheiser, E. J. Stone, H. Koyama, D. S. Yamashita, C. A. Klade, J. Am. Chem. Soc. 1989, 111, 4407-4413; b) S. Cacchi, G. Fabrizi, L. Moro, J. Org. Chem. 1997, 62, 5327-5332; c) D. I. MaGee, J. D. Leach, T. C. Mallais, Tetrahedron Lett. 1997, 38, 1289-1292; d) D. I. MaGee, J. D. Leach, Tetrahedron Lett. 1997, 38, 8129-8132; e) D. I. MaGee, J. D. Leach, S. Setiadji, Tetrahedron 1999, 55, 2847-2856; f) F. Stauffer, R. Neier, Org. Lett. 2000, 2, 3535-3537.
44. For the synthesis of 2,3,5-trisubstituted and 2,3,4,5-tetrasubstituted furans, see: a) R. L. Danheiser, E. J. Stone, H. Koyama, D. S. Yamashita, C. A. Klade, J. Am. Chem. Soc. 1989, 111, 4407-4413; b) S. Cacchi, G. Fabrizi, L. Moro, J. Org. Chem. 1997, 62, 5327-5332; c) D. I. MaGee, J. D. Leach, T. C. Mallais, Tetrahedron Lett. 1997, 38, 1289-1292; d) D. I. MaGee, J. D. Leach, Tetrahedron Lett. 1997, 38, 8129-8132; e) D. I. MaGee, J. D. Leach, S. Setiadji, Tetrahedron 1999, 55, 2847-2856; f) F. Stauffer, R. Neier, Org. Lett. 2000, 2, 3535-3537.
45. For the synthesis of 2,3,5-trisubstituted and 2,3,4,5-tetrasubstituted furans, see: a) R. L. Danheiser, E. J. Stone, H. Koyama, D. S. Yamashita, C. A. Klade, J. Am. Chem. Soc. 1989, 111, 4407-4413; b) S. Cacchi, G. Fabrizi, L. Moro, J. Org. Chem. 1997, 62, 5327-5332; c) D. I. MaGee, J. D. Leach, T. C. Mallais, Tetrahedron Lett. 1997, 38, 1289-1292; d) D. I. MaGee, J. D. Leach, Tetrahedron Lett. 1997, 38, 8129-8132; e) D. I. MaGee, J. D. Leach, S. Setiadji, Tetrahedron 1999, 55, 2847-2856; f) F. Stauffer, R. Neier, Org. Lett. 2000, 2, 3535-3537.
46. For the synthesis of 2,3,5-trisubstituted and 2,3,4,5-tetrasubstituted furans, see: a) R. L. Danheiser, E. J. Stone, H. Koyama, D. S. Yamashita, C. A. Klade, J. Am. Chem. Soc. 1989, 111, 4407-4413; b) S. Cacchi, G. Fabrizi, L. Moro, J. Org. Chem. 1997, 62, 5327-5332; c) D. I. MaGee, J. D. Leach, T. C. Mallais, Tetrahedron Lett. 1997, 38, 1289-1292; d) D. I. MaGee, J. D. Leach, Tetrahedron Lett. 1997, 38, 8129-8132; e) D. I. MaGee, J. D. Leach, S. Setiadji, Tetrahedron 1999, 55, 2847-2856; f) F. Stauffer, R. Neier, Org. Lett. 2000, 2, 3535-3537.
47. For the synthesis of 2,3,5-trisubstituted and 2,3,4,5-tetrasubstituted furans, see: a) R. L. Danheiser, E. J. Stone, H. Koyama, D. S. Yamashita, C. A. Klade, J. Am. Chem. Soc. 1989, 111, 4407-4413; b) S. Cacchi, G. Fabrizi, L. Moro, J. Org. Chem. 1997, 62, 5327-5332; c) D. I. MaGee, J. D. Leach, T. C. Mallais, Tetrahedron Lett. 1997, 38, 1289-1292; d) D. I. MaGee, J. D. Leach, Tetrahedron Lett. 1997, 38, 8129-8132; e) D. I. MaGee, J. D. Leach, S. Setiadji, Tetrahedron 1999, 55, 2847-2856; f) F. Stauffer, R. Neier, Org. Lett. 2000, 2, 3535-3537.
48. a) J. A. Marshall, E. D. Robinson, J. Org. Chem. 1990, 55, 3450-3451;
49. b) J. A. Marshall, G. S. Bartley, J. Org. Chem. 1994, 59, 7169-7171;
50. c) J. A. Marshall, E. M. Wallace, J. Org. Chem. 1995, 60, 796-797.
51. a) J. A. Marshall, C. A. Clark, J. Org. Chem. 1997, 62, 4313-4320;
52. b) J. A. Marshall, G. S. Bartley, E. M. Wallace, J. Org. Chem. 1996, 61, 5729-5735.
53. a) A.S. K. Hashmi, Angew. Chem. 1995, 107, 1749-1751; Angew. Chem. Int. Ed. Engl. 1995, 34, 1581-1583;
54. a) A.S. K. Hashmi, Angew. Chem. 1995, 107, 1749-1751; Angew. Chem. Int. Ed. Engl. 1995, 34, 1581-1583;
55. b) A. S. K. Hashmi, T. L. Ruppert, T. Knöfel, J. W. Bats, J. Org. Chem. 1997, 62, 7295-7304.
56. A. S. K. Hashmi, L. Schwarz, J. H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382-2385; Angew. Chem. Int. Ed. 2000, 39, 2285-2288.
57. A. S. K. Hashmi, L. Schwarz, J. H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382-2385; Angew. Chem. Int. Ed. 2000, 39, 2285-2288.
58. S. Ma, Z. Yu, Angew. Chem. 2002, 114, 1853-1856; Angew. Chem. Int. Ed. 2002, 41, 1775-1778.
59. S. Ma, Z. Yu, Angew. Chem. 2002, 114, 1853-1856; Angew. Chem. Int. Ed. 2002, 41, 1775-1778.
60. For some of our most recent results, see: a) S. Ma, W. Gao, Synlett 2002, 65-68; b) S. Ma, Z. Shi, Chem. Commun. 2002, 540-541; c) S. Ma, N. Jiao, S. Zhao, H. Hou, J. Org. Chem. 2002, 67, 2837-2847; d) S. Ma, D. Duan, Y. Wang, J. Comb. Chem. 2002, 4, 239-247; e) S. Ma, W. Gao, J. Org. Chem. 2002, 67, 6104-6112; f) S. Ma, H. Xie, J. Org. Chem. 2002, 67, 6575-6578; g) S. Ma, W. Gao, Org. Lett. 2002, 4, 2989-2992.
61. For some of our most recent results, see: a) S. Ma, W. Gao, Synlett 2002, 65-68; b) S. Ma, Z. Shi, Chem. Commun. 2002, 540-541; c) S. Ma, N. Jiao, S. Zhao, H. Hou, J. Org. Chem. 2002, 67, 2837-2847; d) S. Ma, D. Duan, Y. Wang, J. Comb. Chem. 2002, 4, 239-247; e) S. Ma, W. Gao, J. Org. Chem. 2002, 67, 6104-6112; f) S. Ma, H. Xie, J. Org. Chem. 2002, 67, 6575-6578; g) S. Ma, W. Gao, Org. Lett. 2002, 4, 2989-2992.
62. For some of our most recent results, see: a) S. Ma, W. Gao, Synlett 2002, 65-68; b) S. Ma, Z. Shi, Chem. Commun. 2002, 540-541; c) S. Ma, N. Jiao, S. Zhao, H. Hou, J. Org. Chem. 2002, 67, 2837-2847; d) S. Ma, D. Duan, Y. Wang, J. Comb. Chem. 2002, 4, 239-247; e) S. Ma, W. Gao, J. Org. Chem. 2002, 67, 6104-6112; f) S. Ma, H. Xie, J. Org. Chem. 2002, 67, 6575-6578; g) S. Ma, W. Gao, Org. Lett. 2002, 4, 2989-2992.
63. For some of our most recent results, see: a) S. Ma, W. Gao, Synlett 2002, 65-68; b) S. Ma, Z. Shi, Chem. Commun. 2002, 540-541; c) S. Ma, N. Jiao, S. Zhao, H. Hou, J. Org. Chem. 2002, 67, 2837-2847; d) S. Ma, D. Duan, Y. Wang, J. Comb. Chem. 2002, 4, 239-247; e) S. Ma, W. Gao, J. Org. Chem. 2002, 67, 6104-6112; f) S. Ma, H. Xie, J. Org. Chem. 2002, 67, 6575-6578; g) S. Ma, W. Gao, Org. Lett. 2002, 4, 2989-2992.
64. For some of our most recent results, see: a) S. Ma, W. Gao, Synlett 2002, 65-68; b) S. Ma, Z. Shi, Chem. Commun. 2002, 540-541; c) S. Ma, N. Jiao, S. Zhao, H. Hou, J. Org. Chem. 2002, 67, 2837-2847; d) S. Ma, D. Duan, Y. Wang, J. Comb. Chem. 2002, 4, 239-247; e) S. Ma, W. Gao, J. Org. Chem. 2002, 67, 6104-6112; f) S. Ma, H. Xie, J. Org. Chem. 2002, 67, 6575-6578; g) S. Ma, W. Gao, Org. Lett. 2002, 4, 2989-2992.
65. For some of our most recent results, see: a) S. Ma, W. Gao, Synlett 2002, 65-68; b) S. Ma, Z. Shi, Chem. Commun. 2002, 540-541; c) S. Ma, N. Jiao, S. Zhao, H. Hou, J. Org. Chem. 2002, 67, 2837-2847; d) S. Ma, D. Duan, Y. Wang, J. Comb. Chem. 2002, 4, 239-247; e) S. Ma, W. Gao, J. Org. Chem. 2002, 67, 6104-6112; f) S. Ma, H. Xie, J. Org. Chem. 2002, 67, 6575-6578; g) S. Ma, W. Gao, Org. Lett. 2002, 4, 2989-2992.
66. For some of our most recent results, see: a) S. Ma, W. Gao, Synlett 2002, 65-68; b) S. Ma, Z. Shi, Chem. Commun. 2002, 540-541; c) S. Ma, N. Jiao, S. Zhao, H. Hou, J. Org. Chem. 2002, 67, 2837-2847; d) S. Ma, D. Duan, Y. Wang, J. Comb. Chem. 2002, 4, 239-247; e) S. Ma, W. Gao, J. Org. Chem. 2002, 67, 6104-6112; f) S. Ma, H. Xie, J. Org. Chem. 2002, 67, 6575-6578; g) S. Ma, W. Gao, Org. Lett. 2002, 4, 2989-2992.
67. For palladium-catalyzed cross-coupling cyclization of allylic bromides with 1,2-allenyl ketones, see: S. Ma. L. Li, Org. Lett. 2000, 2, 941-944.
68. S. Ma, J. Zhang, Chem. Commun. 2000, 117-118.
69. For a review of the synthesis of 1,2-allenyl ketones, see: a) L. Li. S. Ma, Chin. J. Org. Chem. 2000, 20, 850-860; b) S. Ma, L. Li, H. Xie, J. Org. Chem. 1999, 64, 5325-5328.
70. For a review of the synthesis of 1,2-allenyl ketones, see: a) L. Li. S. Ma, Chin. J. Org. Chem. 2000, 20, 850-860; b) S. Ma, L. Li, H. Xie, J. Org. Chem. 1999, 64, 5325-5328.
71. N. A. Petasis, K. A. Teets, J. Am. Chem. Soc. 1992, 114, 10328-10334.
72. The products are very air sensitive, and their structure analysis should be performed under Ar.
73. Certain tetrasubstituted furans show high estrogen-receptor (ER) binding selectivity, see: D. S. Mortensen, A. L. Rodriguez, K. E. Carlson, J. Sun, B. S. Katzenellenbogen, J. A. Katzenellenbogen, J. Med. Chem. 2001, 44, 3838-3848.
74. F. Y. Kwong, K. S. Chan. Chem. Commun. 2000, 1069-1070.
75. a) N. Yoshimura, S. I. Murahashi, I. Moritani, J. Organomet. Chem. 1973, 52, C58-60
76. b) Z. Wang, Z. Zhang, X. Lu, Organometallics 2000, 19, 775-780.
77. S. Ma, S. Wu, Tetrahedron Lett. 2001, 42, 4075-4077.
78. P. L. Piaux, M. Gaudemar, L. Henry, Bull. Soc. Chim. Fr. 1956, 794-795.
79. G. G. Melikyan, V. M. Mkrtchyan, S. O. Budanyan, O. Vostrowsky, H. J. Bestmann, Chem. Ber. 1991, 2037-2040.
80. L. Alcaraz, J. J. Hamett, C. Mioskowski, J. P. Martel, T. L. Gall, D. S. Shin, J. R. Falck, Tetrahedron Lett. 1994, 35, 5453-5456.