Synthesis of Functionalized Heteroaromatics: Application to Formal Total Synthesis of Camptothecin

Synlett

Volumn 1997, Issue 3, 1997, Pages 298-300

  Murata, Naoko ^a   Sugihara, Takumichi ^a   Kondo, Yoshinori ^a   Sakamoto, Takao ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042881856     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-785     Document Type: Article

References (39)

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4. Our previous work along this line, see: a) Sakamoto, T.; Kondo, Y.; Murata, N.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 5373. b) Sakamoto, T.; Kondo, Y.; Murata, N.; Yamanaka, H. Tetrahedron, 1993, 49, 9713. c) Kondo, Y.; Murata, N.; Sakamoto, T. Heterocycles, 1994, 37, 1467.
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13. For the typical reviews: a) Schlty, A. G. Chem. Rev. 1973, 73, 385. b) Hutchinson, C. R. Tetrahedron, 1981, 37, 1047. c) Cia, J. C.; Hutchinson, C. R. Chem. Heterocycl. Compd. 1983, 25, 753. d) Cia, J. C.; Hutchinson, C. R. The Alkaloids. Chemistry and Pharmacology; Brossi, A. Ed.; Academic Press, Inc.: New York, 1983, vol. 21, p. 101. e) Curran, D. P.; Sisko, J.; Yeske, P. E.; Liu, H. Pure Appl. Chem. 1993, 65, 1153.
14. For the typical reviews: a) Schlty, A. G. Chem. Rev. 1973, 73, 385. b) Hutchinson, C. R. Tetrahedron, 1981, 37, 1047. c) Cia, J. C.; Hutchinson, C. R. Chem. Heterocycl. Compd. 1983, 25, 753. d) Cia, J. C.; Hutchinson, C. R. The Alkaloids. Chemistry and Pharmacology; Brossi, A. Ed.; Academic Press, Inc.: New York, 1983, vol. 21, p. 101. e) Curran, D. P.; Sisko, J.; Yeske, P. E.; Liu, H. Pure Appl. Chem. 1993, 65, 1153.
15. For the typical reviews: a) Schlty, A. G. Chem. Rev. 1973, 73, 385. b) Hutchinson, C. R. Tetrahedron, 1981, 37, 1047. c) Cia, J. C.; Hutchinson, C. R. Chem. Heterocycl. Compd. 1983, 25, 753. d) Cia, J. C.; Hutchinson, C. R. The Alkaloids. Chemistry and Pharmacology; Brossi, A. Ed.; Academic Press, Inc.: New York, 1983, vol. 21, p. 101. e) Curran, D. P.; Sisko, J.; Yeske, P. E.; Liu, H. Pure Appl. Chem. 1993, 65, 1153.
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18. For the recent synthetic studies, see: a) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863. b) Comins, D. L.; Buevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971. c) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611. d) Rao, A. V. R.; Yadav, J. S.; Valluri, M. Tetrahedron Lett. 1994, 35, 3613. e) Comins, D. L.; Hong, H.; Saha, J. K.; Jianhua, G. J. Org. Chem. 1994, 59, 5120. f) Curran, D. P.; Ko, S.-B. J. Org. Chem. 1994, 59, 6139. g) Snyder, L.; Shen, W.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 7033. h) Jew, S.-s.; OK, K.-d.; Kim, H.-j.; Kim, M. G.; Kim, J. M.; Hah, J. M.; Cho, Y.-s. Tetrahedron: Asymmetry, 1995, 6, 1245. i) Luzzio, M. J.; Besterman, J. M.; Emerson, D. L.; Evans, M. G.; Lackey, K.; Leitner, P. L.; MsIntyre, G.; Morton, B.; Myers, P. L.; Peel, M.; Sisco, J. M.; Sternbach, D. D.; Tong, W.-Q.; Truesdale, A.; Uehling, D. E.; Vuong, A.; Yates, J. J. Med. Chem. 1995, 38, 395. j) Ciufolini, M. A.; Roschangar, F. Angew. Chem. Int. Ed. Engl. 1996, 35, 1692, and references cited therein.
19. For the recent synthetic studies, see: a) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863. b) Comins, D. L.; Buevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971. c) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611. d) Rao, A. V. R.; Yadav, J. S.; Valluri, M. Tetrahedron Lett. 1994, 35, 3613. e) Comins, D. L.; Hong, H.; Saha, J. K.; Jianhua, G. J. Org. Chem. 1994, 59, 5120. f) Curran, D. P.; Ko, S.-B. J. Org. Chem. 1994, 59, 6139. g) Snyder, L.; Shen, W.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 7033. h) Jew, S.-s.; OK, K.-d.; Kim, H.-j.; Kim, M. G.; Kim, J. M.; Hah, J. M.; Cho, Y.-s. Tetrahedron: Asymmetry, 1995, 6, 1245. i) Luzzio, M. J.; Besterman, J. M.; Emerson, D. L.; Evans, M. G.; Lackey, K.; Leitner, P. L.; MsIntyre, G.; Morton, B.; Myers, P. L.; Peel, M.; Sisco, J. M.; Sternbach, D. D.; Tong, W.-Q.; Truesdale, A.; Uehling, D. E.; Vuong, A.; Yates, J. J. Med. Chem. 1995, 38, 395. j) Ciufolini, M. A.; Roschangar, F. Angew. Chem. Int. Ed. Engl. 1996, 35, 1692, and references cited therein.
20. For the recent synthetic studies, see: a) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863. b) Comins, D. L.; Buevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971. c) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611. d) Rao, A. V. R.; Yadav, J. S.; Valluri, M. Tetrahedron Lett. 1994, 35, 3613. e) Comins, D. L.; Hong, H.; Saha, J. K.; Jianhua, G. J. Org. Chem. 1994, 59, 5120. f) Curran, D. P.; Ko, S.-B. J. Org. Chem. 1994, 59, 6139. g) Snyder, L.; Shen, W.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 7033. h) Jew, S.-s.; OK, K.-d.; Kim, H.-j.; Kim, M. G.; Kim, J. M.; Hah, J. M.; Cho, Y.-s. Tetrahedron: Asymmetry, 1995, 6, 1245. i) Luzzio, M. J.; Besterman, J. M.; Emerson, D. L.; Evans, M. G.; Lackey, K.; Leitner, P. L.; MsIntyre, G.; Morton, B.; Myers, P. L.; Peel, M.; Sisco, J. M.; Sternbach, D. D.; Tong, W.-Q.; Truesdale, A.; Uehling, D. E.; Vuong, A.; Yates, J. J. Med. Chem. 1995, 38, 395. j) Ciufolini, M. A.; Roschangar, F. Angew. Chem. Int. Ed. Engl. 1996, 35, 1692, and references cited therein.
21. For the recent synthetic studies, see: a) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863. b) Comins, D. L.; Buevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971. c) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611. d) Rao, A. V. R.; Yadav, J. S.; Valluri, M. Tetrahedron Lett. 1994, 35, 3613. e) Comins, D. L.; Hong, H.; Saha, J. K.; Jianhua, G. J. Org. Chem. 1994, 59, 5120. f) Curran, D. P.; Ko, S.-B. J. Org. Chem. 1994, 59, 6139. g) Snyder, L.; Shen, W.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 7033. h) Jew, S.-s.; OK, K.-d.; Kim, H.-j.; Kim, M. G.; Kim, J. M.; Hah, J. M.; Cho, Y.-s. Tetrahedron: Asymmetry, 1995, 6, 1245. i) Luzzio, M. J.; Besterman, J. M.; Emerson, D. L.; Evans, M. G.; Lackey, K.; Leitner, P. L.; MsIntyre, G.; Morton, B.; Myers, P. L.; Peel, M.; Sisco, J. M.; Sternbach, D. D.; Tong, W.-Q.; Truesdale, A.; Uehling, D. E.; Vuong, A.; Yates, J. J. Med. Chem. 1995, 38, 395. j) Ciufolini, M. A.; Roschangar, F. Angew. Chem. Int. Ed. Engl. 1996, 35, 1692, and references cited therein.
22. For the recent synthetic studies, see: a) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863. b) Comins, D. L.; Buevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971. c) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611. d) Rao, A. V. R.; Yadav, J. S.; Valluri, M. Tetrahedron Lett. 1994, 35, 3613. e) Comins, D. L.; Hong, H.; Saha, J. K.; Jianhua, G. J. Org. Chem. 1994, 59, 5120. f) Curran, D. P.; Ko, S.-B. J. Org. Chem. 1994, 59, 6139. g) Snyder, L.; Shen, W.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 7033. h) Jew, S.-s.; OK, K.-d.; Kim, H.-j.; Kim, M. G.; Kim, J. M.; Hah, J. M.; Cho, Y.-s. Tetrahedron: Asymmetry, 1995, 6, 1245. i) Luzzio, M. J.; Besterman, J. M.; Emerson, D. L.; Evans, M. G.; Lackey, K.; Leitner, P. L.; MsIntyre, G.; Morton, B.; Myers, P. L.; Peel, M.; Sisco, J. M.; Sternbach, D. D.; Tong, W.-Q.; Truesdale, A.; Uehling, D. E.; Vuong, A.; Yates, J. J. Med. Chem. 1995, 38, 395. j) Ciufolini, M. A.; Roschangar, F. Angew. Chem. Int. Ed. Engl. 1996, 35, 1692, and references cited therein.
23. For the recent synthetic studies, see: a) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863. b) Comins, D. L.; Buevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971. c) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611. d) Rao, A. V. R.; Yadav, J. S.; Valluri, M. Tetrahedron Lett. 1994, 35, 3613. e) Comins, D. L.; Hong, H.; Saha, J. K.; Jianhua, G. J. Org. Chem. 1994, 59, 5120. f) Curran, D. P.; Ko, S.-B. J. Org. Chem. 1994, 59, 6139. g) Snyder, L.; Shen, W.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 7033. h) Jew, S.-s.; OK, K.-d.; Kim, H.-j.; Kim, M. G.; Kim, J. M.; Hah, J. M.; Cho, Y.-s. Tetrahedron: Asymmetry, 1995, 6, 1245. i) Luzzio, M. J.; Besterman, J. M.; Emerson, D. L.; Evans, M. G.; Lackey, K.; Leitner, P. L.; MsIntyre, G.; Morton, B.; Myers, P. L.; Peel, M.; Sisco, J. M.; Sternbach, D. D.; Tong, W.-Q.; Truesdale, A.; Uehling, D. E.; Vuong, A.; Yates, J. J. Med. Chem. 1995, 38, 395. j) Ciufolini, M. A.; Roschangar, F. Angew. Chem. Int. Ed. Engl. 1996, 35, 1692, and references cited therein.
24. For the recent synthetic studies, see: a) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863. b) Comins, D. L.; Buevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971. c) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611. d) Rao, A. V. R.; Yadav, J. S.; Valluri, M. Tetrahedron Lett. 1994, 35, 3613. e) Comins, D. L.; Hong, H.; Saha, J. K.; Jianhua, G. J. Org. Chem. 1994, 59, 5120. f) Curran, D. P.; Ko, S.-B. J. Org. Chem. 1994, 59, 6139. g) Snyder, L.; Shen, W.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 7033. h) Jew, S.-s.; OK, K.-d.; Kim, H.-j.; Kim, M. G.; Kim, J. M.; Hah, J. M.; Cho, Y.-s. Tetrahedron: Asymmetry, 1995, 6, 1245. i) Luzzio, M. J.; Besterman, J. M.; Emerson, D. L.; Evans, M. G.; Lackey, K.; Leitner, P. L.; MsIntyre, G.; Morton, B.; Myers, P. L.; Peel, M.; Sisco, J. M.; Sternbach, D. D.; Tong, W.-Q.; Truesdale, A.; Uehling, D. E.; Vuong, A.; Yates, J. J. Med. Chem. 1995, 38, 395. j) Ciufolini, M. A.; Roschangar, F. Angew. Chem. Int. Ed. Engl. 1996, 35, 1692, and references cited therein.
25. For the recent synthetic studies, see: a) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863. b) Comins, D. L.; Buevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971. c) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611. d) Rao, A. V. R.; Yadav, J. S.; Valluri, M. Tetrahedron Lett. 1994, 35, 3613. e) Comins, D. L.; Hong, H.; Saha, J. K.; Jianhua, G. J. Org. Chem. 1994, 59, 5120. f) Curran, D. P.; Ko, S.-B. J. Org. Chem. 1994, 59, 6139. g) Snyder, L.; Shen, W.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 7033. h) Jew, S.-s.; OK, K.-d.; Kim, H.-j.; Kim, M. G.; Kim, J. M.; Hah, J. M.; Cho, Y.-s. Tetrahedron: Asymmetry, 1995, 6, 1245. i) Luzzio, M. J.; Besterman, J. M.; Emerson, D. L.; Evans, M. G.; Lackey, K.; Leitner, P. L.; MsIntyre, G.; Morton, B.; Myers, P. L.; Peel, M.; Sisco, J. M.; Sternbach, D. D.; Tong, W.-Q.; Truesdale, A.; Uehling, D. E.; Vuong, A.; Yates, J. J. Med. Chem. 1995, 38, 395. j) Ciufolini, M. A.; Roschangar, F. Angew. Chem. Int. Ed. Engl. 1996, 35, 1692, and references cited therein.
26. For the recent synthetic studies, see: a) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863. b) Comins, D. L.; Buevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971. c) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611. d) Rao, A. V. R.; Yadav, J. S.; Valluri, M. Tetrahedron Lett. 1994, 35, 3613. e) Comins, D. L.; Hong, H.; Saha, J. K.; Jianhua, G. J. Org. Chem. 1994, 59, 5120. f) Curran, D. P.; Ko, S.-B. J. Org. Chem. 1994, 59, 6139. g) Snyder, L.; Shen, W.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 7033. h) Jew, S.-s.; OK, K.-d.; Kim, H.-j.; Kim, M. G.; Kim, J. M.; Hah, J. M.; Cho, Y.-s. Tetrahedron: Asymmetry, 1995, 6, 1245. i) Luzzio, M. J.; Besterman, J. M.; Emerson, D. L.; Evans, M. G.; Lackey, K.; Leitner, P. L.; MsIntyre, G.; Morton, B.; Myers, P. L.; Peel, M.; Sisco, J. M.; Sternbach, D. D.; Tong, W.-Q.; Truesdale, A.; Uehling, D. E.; Vuong, A.; Yates, J. J. Med. Chem. 1995, 38, 395. j) Ciufolini, M. A.; Roschangar, F. Angew. Chem. Int. Ed. Engl. 1996, 35, 1692, and references cited therein.
27. For the recent synthetic studies, see: a) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863. b) Comins, D. L.; Buevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971. c) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611. d) Rao, A. V. R.; Yadav, J. S.; Valluri, M. Tetrahedron Lett. 1994, 35, 3613. e) Comins, D. L.; Hong, H.; Saha, J. K.; Jianhua, G. J. Org. Chem. 1994, 59, 5120. f) Curran, D. P.; Ko, S.-B. J. Org. Chem. 1994, 59, 6139. g) Snyder, L.; Shen, W.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 7033. h) Jew, S.-s.; OK, K.-d.; Kim, H.-j.; Kim, M. G.; Kim, J. M.; Hah, J. M.; Cho, Y.-s. Tetrahedron: Asymmetry, 1995, 6, 1245. i) Luzzio, M. J.; Besterman, J. M.; Emerson, D. L.; Evans, M. G.; Lackey, K.; Leitner, P. L.; MsIntyre, G.; Morton, B.; Myers, P. L.; Peel, M.; Sisco, J. M.; Sternbach, D. D.; Tong, W.-Q.; Truesdale, A.; Uehling, D. E.; Vuong, A.; Yates, J. J. Med. Chem. 1995, 38, 395. j) Ciufolini, M. A.; Roschangar, F. Angew. Chem. Int. Ed. Engl. 1996, 35, 1692, and references cited therein.
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29. Methyl 2-chloro-3-quinolinecarboxylate was obtained by the oxidative esterification of 2-chloro-3-quinolinecarbaldehyde which was prepared according to the following literature: Meth-Cohn, O.; Rhouati, S.; Tarnowski, B.; Robinson, A. J. J. Chem. Soc., Perkin Trans. 1, 1981, 1537.
30. Recently the Pd-mediated substitution of the chloride in 2-chloroquinolines has been reported: Ciufolini, M. A.; Mitchell, J. W.; Roschangar, F. Tetrahedron Lett. 1996, 37, 8281.
31. For the typical reviews of the Pd-catalyzed carbonylation reactions, see: a) Tsuji, J. Organic Synthesis with Palladium Compounds, Springer-Verlag: Berlin, 1980. b) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic Press, Inc.: New York, 1985. c) Tsuji, J. Palladium Reagents and Catalyst, John Wiley & Sons: Chichester, 1995.
32. For the typical reviews of the Pd-catalyzed carbonylation reactions, see: a) Tsuji, J. Organic Synthesis with Palladium Compounds, Springer-Verlag: Berlin, 1980. b) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic Press, Inc.: New York, 1985. c) Tsuji, J. Palladium Reagents and Catalyst, John Wiley & Sons: Chichester, 1995.
33. For the typical reviews of the Pd-catalyzed carbonylation reactions, see: a) Tsuji, J. Organic Synthesis with Palladium Compounds, Springer-Verlag: Berlin, 1980. b) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic Press, Inc.: New York, 1985. c) Tsuji, J. Palladium Reagents and Catalyst, John Wiley & Sons: Chichester, 1995.
34. a) Cassar, L.; Roa, M.; Gardano, A. J. Organomet. Chem. 1976, 121, C55.
35. b) Alper, H.; Hashem, K.; Heveling, J. Organametallics, 1982, 1, 775.
36. c) Milstein, D. Organometallics. 1982, 1, 882.
37. d) Tsuji, J.; Sato, K.; Okumoto, H. Tetrahedron Lett. 1982, 23, 5189.
38. Recently the Pd-catalyzed carbonylation of propargyl methanesulfonates has been reported, however the process involves isomerization to allenic esters: a) Marshall, J. A.; Wallace, E. M. J. Org. Chem. 1995, 60, 796. b) Marshall, J. A.; Wolf, A. W. J. Org. Chem. 1996, 61, 3238.
39. Recently the Pd-catalyzed carbonylation of propargyl methanesulfonates has been reported, however the process involves isomerization to allenic esters: a) Marshall, J. A.; Wallace, E. M. J. Org. Chem. 1995, 60, 796. b) Marshall, J. A.; Wolf, A. W. J. Org. Chem. 1996, 61, 3238.