Approaches to the cephalotaxine skeleton using an intramolecular heck reaction

Chemical and Pharmaceutical Bulletin

Volumn 46, Issue 7, 1998, Pages 1084-1089

  Ikeda, Masazumi ^a   Hirose, Ken Ichi ^a   El Bialy, Serry A A ^a   Sato, Tatsunori ^a   Yakura, Takayuki ^a   Bayomi, Said M M ^b  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^b MANSOURA UNIVERSITY   (Egypt)

Author keywords

Anti elimination; Cephalotaxine; Cope rearrangement; Intramolecular aldol condensation; Intramolecular Heck reaction; Tandem Heck reaction

Indexed keywords

1 [2 (O IODOPHENYL)ACETYL] 1 AZASPIRO[4.4]NON 8 EN 7 ONE; 1 [2 (O IODOPHENYL)ACETYL] 2 (PROP 2 ENYL) 2 VINYLPYRROLIDINE; 1,2,3,5,6,8,9,13B OCTAHYDRO 2 METHYLENE 4H CYCLOPENTA[A]PYRROLO[2,1 B][3]BENZAZEPIN 8 ONE; 1,3 BIS(DIPHENYLPHOSPHINO)PROPANE; 2,3,5,6,8,9 HEXAHYDRO 4H CYCLOPENTA[A]PYRROLO[2,1 B][3]BENZAZEPINE 2,8 DIONE; ACETONITRILE; BENZAZEPINE DERIVATIVE; CEPHALOTAXINE; HETEROCYCLIC COMPOUND; HEXAHYDRO 1H PYRROLO[2,1 B][3]BENZAZEPIN N5 ONE; N,N DIMETHYLFORMAMIDE; PALLADIUM; PHOSPHINE DERIVATIVE; PYRROLIDINE DERIVATIVE; SILVER DERIVATIVE; TRIBUTYLPHOSPHINE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0031828105     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.1084     Document Type: Article

References (42)

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5. For reviews of the Cephalotaxus alkaloids, see: Huang L., Xue Z., "The Alkaloids-Chemistry and Pharmacology," Vol. 23, ed. by Brossi A., Academic Press, Orland, 1984, pp. 157-226; Smith C. R., Jr., Mikolajczak K. L., Powell R. G., "Anticancer Agents Based on Natural Product Models," ed. by Cassady J. M., Douros J. D., Academic Press, New York, 1980, pp. 391-416; Miah M. A. J., Hudlicky T., Reed J. W., "The Alkaloids-Chemistry and Biology," Vol. 51, ed. by Cordell G. A., Academic Press, San Diego, 1998, pp. 199-269.
6. For reviews of the Cephalotaxus alkaloids, see: Huang L., Xue Z., "The Alkaloids-Chemistry and Pharmacology," Vol. 23, ed. by Brossi A., Academic Press, Orland, 1984, pp. 157-226; Smith C. R., Jr., Mikolajczak K. L., Powell R. G., "Anticancer Agents Based on Natural Product Models," ed. by Cassady J. M., Douros J. D., Academic Press, New York, 1980, pp. 391-416; Miah M. A. J., Hudlicky T., Reed J. W., "The Alkaloids-Chemistry and Biology," Vol. 51, ed. by Cordell G. A., Academic Press, San Diego, 1998, pp. 199-269.
7. For reviews of the Cephalotaxus alkaloids, see: Huang L., Xue Z., "The Alkaloids-Chemistry and Pharmacology," Vol. 23, ed. by Brossi A., Academic Press, Orland, 1984, pp. 157-226; Smith C. R., Jr., Mikolajczak K. L., Powell R. G., "Anticancer Agents Based on Natural Product Models," ed. by Cassady J. M., Douros J. D., Academic Press, New York, 1980, pp. 391-416; Miah M. A. J., Hudlicky T., Reed J. W., "The Alkaloids-Chemistry and Biology," Vol. 51, ed. by Cordell G. A., Academic Press, San Diego, 1998, pp. 199-269.
8. For the synthesis of optically active cephalotaxine, see: a) Isono N., Mori M., J. Org. Chem., 60, 115-119 (1995); b) Nagasaka T., Sato H., Saeki S., Tetrahedron: Asymmetry, 8, 191-194 (1997).
9. For the synthesis of optically active cephalotaxine, see: a) Isono N., Mori M., J. Org. Chem., 60, 115-119 (1995); b) Nagasaka T., Sato H., Saeki S., Tetrahedron: Asymmetry, 8, 191-194 (1997).
10. For other total syntheses of (±)-cephalotaxine, see: a) Weinreb S. M., Auerbach J., J. Am. Chem. Soc., 97, 2503-2506 (1975); b) Semmelhack M. F., Chong B. P., Stauffer R. D., Rogerson T. D., Chong A., Jones L. D., ibid., 97, 2507-2516 (1975); c) Yasuda S., Yamada T., Hanaoka M., Tetrahedron Lett., 27, 2023-2026 (1986); d) Kuehne M. F., Bornmann W. G., Parsons W. H., Spitzer T. D., Blount, J. F., Zubieta J., J. Org. Chem., 53, 3439-3449 (1988); e) Burkholder T. P., Fuchs P. L., J. Am. Chem. Soc., 112, 9601-9613 (1990); f) Ikeda M., Okano M., Kosaka K., Kido M., Ishibashi H., Chem. Pharm. Bull., 41, 276-281 (1993); g) Lin X. D., Kavash R. W., Mariano P. S., J. Org. Chem., 61, 7335-7347 (1996); h) Tietze L. F., Schirok H., Angew. Chem., Int. Ed. Engl., 36, 1124-1125 (1997).
11. For other total syntheses of (±)-cephalotaxine, see: a) Weinreb S. M., Auerbach J., J. Am. Chem. Soc., 97, 2503-2506 (1975); b) Semmelhack M. F., Chong B. P., Stauffer R. D., Rogerson T. D., Chong A., Jones L. D., ibid., 97, 2507-2516 (1975); c) Yasuda S., Yamada T., Hanaoka M., Tetrahedron Lett., 27, 2023-2026 (1986); d) Kuehne M. F., Bornmann W. G., Parsons W. H., Spitzer T. D., Blount, J. F., Zubieta J., J. Org. Chem., 53, 3439-3449 (1988); e) Burkholder T. P., Fuchs P. L., J. Am. Chem. Soc., 112, 9601-9613 (1990); f) Ikeda M., Okano M., Kosaka K., Kido M., Ishibashi H., Chem. Pharm. Bull., 41, 276-281 (1993); g) Lin X. D., Kavash R. W., Mariano P. S., J. Org. Chem., 61, 7335-7347 (1996); h) Tietze L. F., Schirok H., Angew. Chem., Int. Ed. Engl., 36, 1124-1125 (1997).
12. For other total syntheses of (±)-cephalotaxine, see: a) Weinreb S. M., Auerbach J., J. Am. Chem. Soc., 97, 2503-2506 (1975); b) Semmelhack M. F., Chong B. P., Stauffer R. D., Rogerson T. D., Chong A., Jones L. D., ibid., 97, 2507-2516 (1975); c) Yasuda S., Yamada T., Hanaoka M., Tetrahedron Lett., 27, 2023-2026 (1986); d) Kuehne M. F., Bornmann W. G., Parsons W. H., Spitzer T. D., Blount, J. F., Zubieta J., J. Org. Chem., 53, 3439-3449 (1988); e) Burkholder T. P., Fuchs P. L., J. Am. Chem. Soc., 112, 9601-9613 (1990); f) Ikeda M., Okano M., Kosaka K., Kido M., Ishibashi H., Chem. Pharm. Bull., 41, 276-281 (1993); g) Lin X. D., Kavash R. W., Mariano P. S., J. Org. Chem., 61, 7335-7347 (1996); h) Tietze L. F., Schirok H., Angew. Chem., Int. Ed. Engl., 36, 1124-1125 (1997).
13. For other total syntheses of (±)-cephalotaxine, see: a) Weinreb S. M., Auerbach J., J. Am. Chem. Soc., 97, 2503-2506 (1975); b) Semmelhack M. F., Chong B. P., Stauffer R. D., Rogerson T. D., Chong A., Jones L. D., ibid., 97, 2507-2516 (1975); c) Yasuda S., Yamada T., Hanaoka M., Tetrahedron Lett., 27, 2023-2026 (1986); d) Kuehne M. F., Bornmann W. G., Parsons W. H., Spitzer T. D., Blount, J. F., Zubieta J., J. Org. Chem., 53, 3439-3449 (1988); e) Burkholder T. P., Fuchs P. L., J. Am. Chem. Soc., 112, 9601-9613 (1990); f) Ikeda M., Okano M., Kosaka K., Kido M., Ishibashi H., Chem. Pharm. Bull., 41, 276-281 (1993); g) Lin X. D., Kavash R. W., Mariano P. S., J. Org. Chem., 61, 7335-7347 (1996); h) Tietze L. F., Schirok H., Angew. Chem., Int. Ed. Engl., 36, 1124-1125 (1997).
14. For other total syntheses of (±)-cephalotaxine, see: a) Weinreb S. M., Auerbach J., J. Am. Chem. Soc., 97, 2503-2506 (1975); b) Semmelhack M. F., Chong B. P., Stauffer R. D., Rogerson T. D., Chong A., Jones L. D., ibid., 97, 2507-2516 (1975); c) Yasuda S., Yamada T., Hanaoka M., Tetrahedron Lett., 27, 2023-2026 (1986); d) Kuehne M. F., Bornmann W. G., Parsons W. H., Spitzer T. D., Blount, J. F., Zubieta J., J. Org. Chem., 53, 3439-3449 (1988); e) Burkholder T. P., Fuchs P. L., J. Am. Chem. Soc., 112, 9601-9613 (1990); f) Ikeda M., Okano M., Kosaka K., Kido M., Ishibashi H., Chem. Pharm. Bull., 41, 276-281 (1993); g) Lin X. D., Kavash R. W., Mariano P. S., J. Org. Chem., 61, 7335-7347 (1996); h) Tietze L. F., Schirok H., Angew. Chem., Int. Ed. Engl., 36, 1124-1125 (1997).
15. For other total syntheses of (±)-cephalotaxine, see: a) Weinreb S. M., Auerbach J., J. Am. Chem. Soc., 97, 2503-2506 (1975); b) Semmelhack M. F., Chong B. P., Stauffer R. D., Rogerson T. D., Chong A., Jones L. D., ibid., 97, 2507-2516 (1975); c) Yasuda S., Yamada T., Hanaoka M., Tetrahedron Lett., 27, 2023-2026 (1986); d) Kuehne M. F., Bornmann W. G., Parsons W. H., Spitzer T. D., Blount, J. F., Zubieta J., J. Org. Chem., 53, 3439-3449 (1988); e) Burkholder T. P., Fuchs P. L., J. Am. Chem. Soc., 112, 9601-9613 (1990); f) Ikeda M., Okano M., Kosaka K., Kido M., Ishibashi H., Chem. Pharm. Bull., 41, 276-281 (1993); g) Lin X. D., Kavash R. W., Mariano P. S., J. Org. Chem., 61, 7335-7347 (1996); h) Tietze L. F., Schirok H., Angew. Chem., Int. Ed. Engl., 36, 1124-1125 (1997).
16. For other total syntheses of (±)-cephalotaxine, see: a) Weinreb S. M., Auerbach J., J. Am. Chem. Soc., 97, 2503-2506 (1975); b) Semmelhack M. F., Chong B. P., Stauffer R. D., Rogerson T. D., Chong A., Jones L. D., ibid., 97, 2507-2516 (1975); c) Yasuda S., Yamada T., Hanaoka M., Tetrahedron Lett., 27, 2023-2026 (1986); d) Kuehne M. F., Bornmann W. G., Parsons W. H., Spitzer T. D., Blount, J. F., Zubieta J., J. Org. Chem., 53, 3439-3449 (1988); e) Burkholder T. P., Fuchs P. L., J. Am. Chem. Soc., 112, 9601-9613 (1990); f) Ikeda M., Okano M., Kosaka K., Kido M., Ishibashi H., Chem. Pharm. Bull., 41, 276-281 (1993); g) Lin X. D., Kavash R. W., Mariano P. S., J. Org. Chem., 61, 7335-7347 (1996); h) Tietze L. F., Schirok H., Angew. Chem., Int. Ed. Engl., 36, 1124-1125 (1997).
17. For other total syntheses of (±)-cephalotaxine, see: a) Weinreb S. M., Auerbach J., J. Am. Chem. Soc., 97, 2503-2506 (1975); b) Semmelhack M. F., Chong B. P., Stauffer R. D., Rogerson T. D., Chong A., Jones L. D., ibid., 97, 2507-2516 (1975); c) Yasuda S., Yamada T., Hanaoka M., Tetrahedron Lett., 27, 2023-2026 (1986); d) Kuehne M. F., Bornmann W. G., Parsons W. H., Spitzer T. D., Blount, J. F., Zubieta J., J. Org. Chem., 53, 3439-3449 (1988); e) Burkholder T. P., Fuchs P. L., J. Am. Chem. Soc., 112, 9601-9613 (1990); f) Ikeda M., Okano M., Kosaka K., Kido M., Ishibashi H., Chem. Pharm. Bull., 41, 276-281 (1993); g) Lin X. D., Kavash R. W., Mariano P. S., J. Org. Chem., 61, 7335-7347 (1996); h) Tietze L. F., Schirok H., Angew. Chem., Int. Ed. Engl., 36, 1124-1125 (1997).
18. Parts of this work have appeared as preliminary communications: Ikeda M., Akamatsu S., Kugo Y., Sato T., Heterocycles, 42, 155-158 (1996); Ikeda M., Matsubayashi K., Imoto T., Kitao K., Ishibashi H., Sato T., ibid., 38, 1237-1240 (1994).
19. Parts of this work have appeared as preliminary communications: Ikeda M., Akamatsu S., Kugo Y., Sato T., Heterocycles, 42, 155-158 (1996); Ikeda M., Matsubayashi K., Imoto T., Kitao K., Ishibashi H., Sato T., ibid., 38, 1237-1240 (1994).
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23. 4 in ether under reflux for 24h or with diisobutylaluminum hydride in dichloromethane at room temperature for 24 h gave 14 in 64 and 60% yields, respectively.
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27. Harayama T., Akiyama T., Nakano Y., Chem. Pharm. Bull., 45, 1723-1725 (1997).
28. For Pd-catalyzed aryl-enone cyclizations, see: a) Ishibashi H., Ito K., Hirano T., Tabuchi M., Ikeda M., Tetrahedron. 49, 4173-4182 (1993); b) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 36, 7047-7050 (1995); c) Comins D. L., Joseph S. P., Zhang Y.-M., ibid., 37, 793-796 (1996); d) Yoneda R., Kimura T., Kinomoto J., Harusawa S., Kurihara T., J. Heterocycl. Chem., 33, 1909-1913 (1996); e) Gibson S. E., Guillo N., Tozer M. J., Chem. Commun., 1997, 637-638; f) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 34, 5933-5936 (1997). For other examples of the formal anti-elimination. see: Dieck H. A., Heck R. F., J. Organomet. Chem., 93, 259-263 (1975); Amos P. C., Whiting D. A., J. Chem. Soc., Chem. Commun., 1987, 510-511; Grigg R., Sridharan V., Stevenson P., Sukirthalingam S., Worakun T., Tetrahedron, 46, 4003-4018 (1990); McIntosh M. C., Weinreb S. M., J. Org. Chem., 58, 4823-4832 (1993); Grigg R., Fretwell P., Meerholtz C., Sridharan V., Tetrahedron, 50, 359-370 (1994).
29. For Pd-catalyzed aryl-enone cyclizations, see: a) Ishibashi H., Ito K., Hirano T., Tabuchi M., Ikeda M., Tetrahedron. 49, 4173-4182 (1993); b) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 36, 7047-7050 (1995); c) Comins D. L., Joseph S. P., Zhang Y.-M., ibid., 37, 793-796 (1996); d) Yoneda R., Kimura T., Kinomoto J., Harusawa S., Kurihara T., J. Heterocycl. Chem., 33, 1909-1913 (1996); e) Gibson S. E., Guillo N., Tozer M. J., Chem. Commun., 1997, 637-638; f) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 34, 5933-5936 (1997). For other examples of the formal anti-elimination. see: Dieck H. A., Heck R. F., J. Organomet. Chem., 93, 259-263 (1975); Amos P. C., Whiting D. A., J. Chem. Soc., Chem. Commun., 1987, 510-511; Grigg R., Sridharan V., Stevenson P., Sukirthalingam S., Worakun T., Tetrahedron, 46, 4003-4018 (1990); McIntosh M. C., Weinreb S. M., J. Org. Chem., 58, 4823-4832 (1993); Grigg R., Fretwell P., Meerholtz C., Sridharan V., Tetrahedron, 50, 359-370 (1994).
30. For Pd-catalyzed aryl-enone cyclizations, see: a) Ishibashi H., Ito K., Hirano T., Tabuchi M., Ikeda M., Tetrahedron. 49, 4173-4182 (1993); b) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 36, 7047-7050 (1995); c) Comins D. L., Joseph S. P., Zhang Y.-M., ibid., 37, 793-796 (1996); d) Yoneda R., Kimura T., Kinomoto J., Harusawa S., Kurihara T., J. Heterocycl. Chem., 33, 1909-1913 (1996); e) Gibson S. E., Guillo N., Tozer M. J., Chem. Commun., 1997, 637-638; f) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 34, 5933-5936 (1997). For other examples of the formal anti-elimination. see: Dieck H. A., Heck R. F., J. Organomet. Chem., 93, 259-263 (1975); Amos P. C., Whiting D. A., J. Chem. Soc., Chem. Commun., 1987, 510-511; Grigg R., Sridharan V., Stevenson P., Sukirthalingam S., Worakun T., Tetrahedron, 46, 4003-4018 (1990); McIntosh M. C., Weinreb S. M., J. Org. Chem., 58, 4823-4832 (1993); Grigg R., Fretwell P., Meerholtz C., Sridharan V., Tetrahedron, 50, 359-370 (1994).
31. For Pd-catalyzed aryl-enone cyclizations, see: a) Ishibashi H., Ito K., Hirano T., Tabuchi M., Ikeda M., Tetrahedron. 49, 4173-4182 (1993); b) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 36, 7047-7050 (1995); c) Comins D. L., Joseph S. P., Zhang Y.-M., ibid., 37, 793-796 (1996); d) Yoneda R., Kimura T., Kinomoto J., Harusawa S., Kurihara T., J. Heterocycl. Chem., 33, 1909-1913 (1996); e) Gibson S. E., Guillo N., Tozer M. J., Chem. Commun., 1997, 637-638; f) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 34, 5933-5936 (1997). For other examples of the formal anti-elimination. see: Dieck H. A., Heck R. F., J. Organomet. Chem., 93, 259-263 (1975); Amos P. C., Whiting D. A., J. Chem. Soc., Chem. Commun., 1987, 510-511; Grigg R., Sridharan V., Stevenson P., Sukirthalingam S., Worakun T., Tetrahedron, 46, 4003-4018 (1990); McIntosh M. C., Weinreb S. M., J. Org. Chem., 58, 4823-4832 (1993); Grigg R., Fretwell P., Meerholtz C., Sridharan V., Tetrahedron, 50, 359-370 (1994).
32. For Pd-catalyzed aryl-enone cyclizations, see: a) Ishibashi H., Ito K., Hirano T., Tabuchi M., Ikeda M., Tetrahedron. 49, 4173-4182 (1993); b) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 36, 7047-7050 (1995); c) Comins D. L., Joseph S. P., Zhang Y.-M., ibid., 37, 793-796 (1996); d) Yoneda R., Kimura T., Kinomoto J., Harusawa S., Kurihara T., J. Heterocycl. Chem., 33, 1909-1913 (1996); e) Gibson S. E., Guillo N., Tozer M. J., Chem. Commun., 1997, 637-638; f) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 34, 5933-5936 (1997). For other examples of the formal anti-elimination. see: Dieck H. A., Heck R. F., J. Organomet. Chem., 93, 259-263 (1975); Amos P. C., Whiting D. A., J. Chem. Soc., Chem. Commun., 1987, 510-511; Grigg R., Sridharan V., Stevenson P., Sukirthalingam S., Worakun T., Tetrahedron, 46, 4003-4018 (1990); McIntosh M. C., Weinreb S. M., J. Org. Chem., 58, 4823-4832 (1993); Grigg R., Fretwell P., Meerholtz C., Sridharan V., Tetrahedron, 50, 359-370 (1994).
33. For Pd-catalyzed aryl-enone cyclizations, see: a) Ishibashi H., Ito K., Hirano T., Tabuchi M., Ikeda M., Tetrahedron. 49, 4173-4182 (1993); b) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 36, 7047-7050 (1995); c) Comins D. L., Joseph S. P., Zhang Y.-M., ibid., 37, 793-796 (1996); d) Yoneda R., Kimura T., Kinomoto J., Harusawa S., Kurihara T., J. Heterocycl. Chem., 33, 1909-1913 (1996); e) Gibson S. E., Guillo N., Tozer M. J., Chem. Commun., 1997, 637-638; f) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 34, 5933-5936 (1997). For other examples of the formal anti-elimination. see: Dieck H. A., Heck R. F., J. Organomet. Chem., 93, 259-263 (1975); Amos P. C., Whiting D. A., J. Chem. Soc., Chem. Commun., 1987, 510-511; Grigg R., Sridharan V., Stevenson P., Sukirthalingam S., Worakun T., Tetrahedron, 46, 4003-4018 (1990); McIntosh M. C., Weinreb S. M., J. Org. Chem., 58, 4823-4832 (1993); Grigg R., Fretwell P., Meerholtz C., Sridharan V., Tetrahedron, 50, 359-370 (1994).
34. For Pd-catalyzed aryl-enone cyclizations, see: a) Ishibashi H., Ito K., Hirano T., Tabuchi M., Ikeda M., Tetrahedron. 49, 4173-4182 (1993); b) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 36, 7047-7050 (1995); c) Comins D. L., Joseph S. P., Zhang Y.-M., ibid., 37, 793-796 (1996); d) Yoneda R., Kimura T., Kinomoto J., Harusawa S., Kurihara T., J. Heterocycl. Chem., 33, 1909-1913 (1996); e) Gibson S. E., Guillo N., Tozer M. J., Chem. Commun., 1997, 637-638; f) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 34, 5933-5936 (1997). For other examples of the formal anti-elimination. see: Dieck H. A., Heck R. F., J. Organomet. Chem., 93, 259-263 (1975); Amos P. C., Whiting D. A., J. Chem. Soc., Chem. Commun., 1987, 510-511; Grigg R., Sridharan V., Stevenson P., Sukirthalingam S., Worakun T., Tetrahedron, 46, 4003-4018 (1990); McIntosh M. C., Weinreb S. M., J. Org. Chem., 58, 4823-4832 (1993); Grigg R., Fretwell P., Meerholtz C., Sridharan V., Tetrahedron, 50, 359-370 (1994).
35. For Pd-catalyzed aryl-enone cyclizations, see: a) Ishibashi H., Ito K., Hirano T., Tabuchi M., Ikeda M., Tetrahedron. 49, 4173-4182 (1993); b) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 36, 7047-7050 (1995); c) Comins D. L., Joseph S. P., Zhang Y.-M., ibid., 37, 793-796 (1996); d) Yoneda R., Kimura T., Kinomoto J., Harusawa S., Kurihara T., J. Heterocycl. Chem., 33, 1909-1913 (1996); e) Gibson S. E., Guillo N., Tozer M. J., Chem. Commun., 1997, 637-638; f) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 34, 5933-5936 (1997). For other examples of the formal anti-elimination. see: Dieck H. A., Heck R. F., J. Organomet. Chem., 93, 259-263 (1975); Amos P. C., Whiting D. A., J. Chem. Soc., Chem. Commun., 1987, 510-511; Grigg R., Sridharan V., Stevenson P., Sukirthalingam S., Worakun T., Tetrahedron, 46, 4003-4018 (1990); McIntosh M. C., Weinreb S. M., J. Org. Chem., 58, 4823-4832 (1993); Grigg R., Fretwell P., Meerholtz C., Sridharan V., Tetrahedron, 50, 359-370 (1994).
36. For Pd-catalyzed aryl-enone cyclizations, see: a) Ishibashi H., Ito K., Hirano T., Tabuchi M., Ikeda M., Tetrahedron. 49, 4173-4182 (1993); b) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 36, 7047-7050 (1995); c) Comins D. L., Joseph S. P., Zhang Y.-M., ibid., 37, 793-796 (1996); d) Yoneda R., Kimura T., Kinomoto J., Harusawa S., Kurihara T., J. Heterocycl. Chem., 33, 1909-1913 (1996); e) Gibson S. E., Guillo N., Tozer M. J., Chem. Commun., 1997, 637-638; f) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 34, 5933-5936 (1997). For other examples of the formal anti-elimination. see: Dieck H. A., Heck R. F., J. Organomet. Chem., 93, 259-263 (1975); Amos P. C., Whiting D. A., J. Chem. Soc., Chem. Commun., 1987, 510-511; Grigg R., Sridharan V., Stevenson P., Sukirthalingam S., Worakun T., Tetrahedron, 46, 4003-4018 (1990); McIntosh M. C., Weinreb S. M., J. Org. Chem., 58, 4823-4832 (1993); Grigg R., Fretwell P., Meerholtz C., Sridharan V., Tetrahedron, 50, 359-370 (1994).
37. For Pd-catalyzed aryl-enone cyclizations, see: a) Ishibashi H., Ito K., Hirano T., Tabuchi M., Ikeda M., Tetrahedron. 49, 4173-4182 (1993); b) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 36, 7047-7050 (1995); c) Comins D. L., Joseph S. P., Zhang Y.-M., ibid., 37, 793-796 (1996); d) Yoneda R., Kimura T., Kinomoto J., Harusawa S., Kurihara T., J. Heterocycl. Chem., 33, 1909-1913 (1996); e) Gibson S. E., Guillo N., Tozer M. J., Chem. Commun., 1997, 637-638; f) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 34, 5933-5936 (1997). For other examples of the formal anti-elimination. see: Dieck H. A., Heck R. F., J. Organomet. Chem., 93, 259-263 (1975); Amos P. C., Whiting D. A., J. Chem. Soc., Chem. Commun., 1987, 510-511; Grigg R., Sridharan V., Stevenson P., Sukirthalingam S., Worakun T., Tetrahedron, 46, 4003-4018 (1990); McIntosh M. C., Weinreb S. M., J. Org. Chem., 58, 4823-4832 (1993); Grigg R., Fretwell P., Meerholtz C., Sridharan V., Tetrahedron, 50, 359-370 (1994).
38. For Pd-catalyzed aryl-enone cyclizations, see: a) Ishibashi H., Ito K., Hirano T., Tabuchi M., Ikeda M., Tetrahedron. 49, 4173-4182 (1993); b) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 36, 7047-7050 (1995); c) Comins D. L., Joseph S. P., Zhang Y.-M., ibid., 37, 793-796 (1996); d) Yoneda R., Kimura T., Kinomoto J., Harusawa S., Kurihara T., J. Heterocycl. Chem., 33, 1909-1913 (1996); e) Gibson S. E., Guillo N., Tozer M. J., Chem. Commun., 1997, 637-638; f) Friestad G. K., Branchaud B. P., Tetrahedron Lett., 34, 5933-5936 (1997). For other examples of the formal anti-elimination. see: Dieck H. A., Heck R. F., J. Organomet. Chem., 93, 259-263 (1975); Amos P. C., Whiting D. A., J. Chem. Soc., Chem. Commun., 1987, 510-511; Grigg R., Sridharan V., Stevenson P., Sukirthalingam S., Worakun T., Tetrahedron, 46, 4003-4018 (1990); McIntosh M. C., Weinreb S. M., J. Org. Chem., 58, 4823-4832 (1993); Grigg R., Fretwell P., Meerholtz C., Sridharan V., Tetrahedron, 50, 359-370 (1994).
39. The authors have deposited the atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained on request from The Director, Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, U.K.
40. MITHRIL84: Gilmore C. J. (1984). An integrated direct methods computer program. Univ. of Glasgow, Scotland.
41. Cromer D. T., Waber J. T., "International Tables for X-ray Crystallography," Vol. 4, The Kynoch Press, Birmingham, 1974, Table 2.2 A.
42. teXan: Crystal Structure Analysis Package, Molecular Structure Corporation (1985 and 1992).