Total synthesis of an antitumor agent RA-VII via an efficient preparation of cycloisodityrosine

Journal of Organic Chemistry

Volumn 64, Issue 17, 1999, Pages 6283-6296

  Bigot, Antony ^a   Tran Huu Dau, Marie Elise ^a   Zhu, Jieping ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CYCLOISODITYROSINE; HEXAPEPTIDE; PEPTIDE DERIVATIVE; RA 7; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0345425777     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990432w     Document Type: Article

References (100)

1. (a) Itokawa, H.; Takeya, K.; Mihara, K.; Mori, N.; Hamanaka, T.; Sonobe, T. Chem. Pharm. Bull. 1983, 31, 1424-1427.
2. (b) Itokawa, H.; Takeya, K.; Mori, N.; Hamanaka, T.; Sonobe, T.; Mihara, K. Chem. Pharm. Bull. 1984, 32, 284-290.
3. (a) Jolad, S. D.; Hoffman, J. J.; Torrance, S. J.; Wiedhopf, R. M.; Cole, J. R.; Arora, S. K.; Bates, R. B.; Gargiulo, R. L.; Kriek, G. R. J. Am. Chem. Soc. 1977, 99, 8040-44.
4. (b) Bates, R. B.; Cole, J. R.; Hoffmann, J. J.; Kriek, G. R.; Linz, G. S.; Torrance, S, J. J. Am. Chem. Soc. 1983, 105, 1343-1347.
5. (a) Itokawa, H.; Takeya, K. Heterocycles 1993, 35, 1467-1501.
6. (b) Itokawa, H.; Takeya, K.; Hitotsuyanagi, Y.; Monta, H. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1997; Vol. 49, pp 301-387.
7. (a) Zalacain, M.; Zaera, E.; Vazquez, D.; Jimenez, A. FEBS Lett. 1982, 148, 95.
8. (b) Morita, H.; Yamamiya, T.; Takeya, K.; Itokawa, H.; Sakuma, C.; Yamada, J.; Suga, T. Chem. Pharm. Bull. 1993, 41, 781-783.
9. Sirdeshpande, B. V.; Toogood, P. L. Bioorg. Chem. 1995, 23, 460-470.
10. Selected examples: (a) Monta, H.; Kondo, K.; Hitotsuyanagi, Y.; Takeya, K.; Itokawa, H.; Tomioka, N.; Itai, A.; Iitaka, Y. Tetrahedron 1991, 47, 2757-2772. (b) Hitotsuyanagi, Y.; Kondo, K.; Takeya, K.; Itokawa, H. Tetrahedron Lett. 1994, 35, 2191-2194. (c) Hitotsuyanagi, Y.; Lee, S.; Takeya, K.; Itokawa, H. J. Chem. Soc., Chem. Commun. 1996, 503-504. (d) Hitotsuyanagi, Y.; Matsumoto, Y.; Sasaki, S.-I.; Suzuki, J.; Takeya, K.; Yamaguchi, K.; Itokawa, H. J. Chem. Soc., Perkin Trans. 1 1996, 1749-1755. (e) Hitotsuyanagi, Y.; Anazawa, Y.; Yamagishi, T.; Samata, K.; Ichihara, T.; Nanaumi, K.; Okado, N.; Nakaike, S.; Mizumura, M.; Takeya, K.; Itokawa, H. Biorg. Med. Chem. Lett. 1997, 7, 3125-3128 and references therein.
11. Selected examples: (a) Monta, H.; Kondo, K.; Hitotsuyanagi, Y.; Takeya, K.; Itokawa, H.; Tomioka, N.; Itai, A.; Iitaka, Y. Tetrahedron 1991, 47, 2757-2772. (b) Hitotsuyanagi, Y.; Kondo, K.; Takeya, K.; Itokawa, H. Tetrahedron Lett. 1994, 35, 2191-2194. (c) Hitotsuyanagi, Y.; Lee, S.; Takeya, K.; Itokawa, H. J. Chem. Soc., Chem. Commun. 1996, 503-504. (d) Hitotsuyanagi, Y.; Matsumoto, Y.; Sasaki, S.-I.; Suzuki, J.; Takeya, K.; Yamaguchi, K.; Itokawa, H. J. Chem. Soc., Perkin Trans. 1 1996, 1749-1755. (e) Hitotsuyanagi, Y.; Anazawa, Y.; Yamagishi, T.; Samata, K.; Ichihara, T.; Nanaumi, K.; Okado, N.; Nakaike, S.; Mizumura, M.; Takeya, K.; Itokawa, H. Biorg. Med. Chem. Lett. 1997, 7, 3125-3128 and references therein.
12. Selected examples: (a) Monta, H.; Kondo, K.; Hitotsuyanagi, Y.; Takeya, K.; Itokawa, H.; Tomioka, N.; Itai, A.; Iitaka, Y. Tetrahedron 1991, 47, 2757-2772. (b) Hitotsuyanagi, Y.; Kondo, K.; Takeya, K.; Itokawa, H. Tetrahedron Lett. 1994, 35, 2191-2194. (c) Hitotsuyanagi, Y.; Lee, S.; Takeya, K.; Itokawa, H. J. Chem. Soc., Chem. Commun. 1996, 503-504. (d) Hitotsuyanagi, Y.; Matsumoto, Y.; Sasaki, S.-I.; Suzuki, J.; Takeya, K.; Yamaguchi, K.; Itokawa, H. J. Chem. Soc., Perkin Trans. 1 1996, 1749-1755. (e) Hitotsuyanagi, Y.; Anazawa, Y.; Yamagishi, T.; Samata, K.; Ichihara, T.; Nanaumi, K.; Okado, N.; Nakaike, S.; Mizumura, M.; Takeya, K.; Itokawa, H. Biorg. Med. Chem. Lett. 1997, 7, 3125-3128 and references therein.
13. Selected examples: (a) Monta, H.; Kondo, K.; Hitotsuyanagi, Y.; Takeya, K.; Itokawa, H.; Tomioka, N.; Itai, A.; Iitaka, Y. Tetrahedron 1991, 47, 2757-2772. (b) Hitotsuyanagi, Y.; Kondo, K.; Takeya, K.; Itokawa, H. Tetrahedron Lett. 1994, 35, 2191-2194. (c) Hitotsuyanagi, Y.; Lee, S.; Takeya, K.; Itokawa, H. J. Chem. Soc., Chem. Commun. 1996, 503-504. (d) Hitotsuyanagi, Y.; Matsumoto, Y.; Sasaki, S.-I.; Suzuki, J.; Takeya, K.; Yamaguchi, K.; Itokawa, H. J. Chem. Soc., Perkin Trans. 1 1996, 1749-1755. (e) Hitotsuyanagi, Y.; Anazawa, Y.; Yamagishi, T.; Samata, K.; Ichihara, T.; Nanaumi, K.; Okado, N.; Nakaike, S.; Mizumura, M.; Takeya, K.; Itokawa, H. Biorg. Med. Chem. Lett. 1997, 7, 3125-3128 and references therein.
14. Selected examples: (a) Monta, H.; Kondo, K.; Hitotsuyanagi, Y.; Takeya, K.; Itokawa, H.; Tomioka, N.; Itai, A.; Iitaka, Y. Tetrahedron 1991, 47, 2757-2772. (b) Hitotsuyanagi, Y.; Kondo, K.; Takeya, K.; Itokawa, H. Tetrahedron Lett. 1994, 35, 2191-2194. (c) Hitotsuyanagi, Y.; Lee, S.; Takeya, K.; Itokawa, H. J. Chem. Soc., Chem. Commun. 1996, 503-504. (d) Hitotsuyanagi, Y.; Matsumoto, Y.; Sasaki, S.-I.; Suzuki, J.; Takeya, K.; Yamaguchi, K.; Itokawa, H. J. Chem. Soc., Perkin Trans. 1 1996, 1749-1755. (e) Hitotsuyanagi, Y.; Anazawa, Y.; Yamagishi, T.; Samata, K.; Ichihara, T.; Nanaumi, K.; Okado, N.; Nakaike, S.; Mizumura, M.; Takeya, K.; Itokawa, H. Biorg. Med. Chem. Lett. 1997, 7, 3125-3128 and references therein.
15. Selected examples: (a) Boger, D. L.; Yohannes, D.; Meyers, J. B., Jr. J. Org. Chem. 1992, 57, 1319-1321. (b) Boger, D. L.; Patane, M. A.; Jin, Q.; Kitos, P. A. Biorg. Med. Chem. 1994, 2, 85-100. (c) Boger, D. L.; Zhou, J.; Winter, B.; Kites, P. A. Biorg. Med. Chem. 1995, 3, 1679-1593. (d) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7357-7363. (e) Boger, D. L.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7364-7378. (f) Boger, D. L.; Zhou, J. Biorg. Med. Chem. 1996, 4, 1597-1603 and references therein.
16. Selected examples: (a) Boger, D. L.; Yohannes, D.; Meyers, J. B., Jr. J. Org. Chem. 1992, 57, 1319-1321. (b) Boger, D. L.; Patane, M. A.; Jin, Q.; Kitos, P. A. Biorg. Med. Chem. 1994, 2, 85-100. (c) Boger, D. L.; Zhou, J.; Winter, B.; Kites, P. A. Biorg. Med. Chem. 1995, 3, 1679-1593. (d) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7357-7363. (e) Boger, D. L.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7364-7378. (f) Boger, D. L.; Zhou, J. Biorg. Med. Chem. 1996, 4, 1597-1603 and references therein.
17. Selected examples: (a) Boger, D. L.; Yohannes, D.; Meyers, J. B., Jr. J. Org. Chem. 1992, 57, 1319-1321. (b) Boger, D. L.; Patane, M. A.; Jin, Q.; Kitos, P. A. Biorg. Med. Chem. 1994, 2, 85-100. (c) Boger, D. L.; Zhou, J.; Winter, B.; Kites, P. A. Biorg. Med. Chem. 1995, 3, 1679-1593. (d) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7357-7363. (e) Boger, D. L.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7364-7378. (f) Boger, D. L.; Zhou, J. Biorg. Med. Chem. 1996, 4, 1597-1603 and references therein.
18. Selected examples: (a) Boger, D. L.; Yohannes, D.; Meyers, J. B., Jr. J. Org. Chem. 1992, 57, 1319-1321. (b) Boger, D. L.; Patane, M. A.; Jin, Q.; Kitos, P. A. Biorg. Med. Chem. 1994, 2, 85-100. (c) Boger, D. L.; Zhou, J.; Winter, B.; Kites, P. A. Biorg. Med. Chem. 1995, 3, 1679-1593. (d) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7357-7363. (e) Boger, D. L.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7364-7378. (f) Boger, D. L.; Zhou, J. Biorg. Med. Chem. 1996, 4, 1597-1603 and references therein.
19. Selected examples: (a) Boger, D. L.; Yohannes, D.; Meyers, J. B., Jr. J. Org. Chem. 1992, 57, 1319-1321. (b) Boger, D. L.; Patane, M. A.; Jin, Q.; Kitos, P. A. Biorg. Med. Chem. 1994, 2, 85-100. (c) Boger, D. L.; Zhou, J.; Winter, B.; Kites, P. A. Biorg. Med. Chem. 1995, 3, 1679-1593. (d) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7357-7363. (e) Boger, D. L.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7364-7378. (f) Boger, D. L.; Zhou, J. Biorg. Med. Chem. 1996, 4, 1597-1603 and references therein.
20. Selected examples: (a) Boger, D. L.; Yohannes, D.; Meyers, J. B., Jr. J. Org. Chem. 1992, 57, 1319-1321. (b) Boger, D. L.; Patane, M. A.; Jin, Q.; Kitos, P. A. Biorg. Med. Chem. 1994, 2, 85-100. (c) Boger, D. L.; Zhou, J.; Winter, B.; Kites, P. A. Biorg. Med. Chem. 1995, 3, 1679-1593. (d) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7357-7363. (e) Boger, D. L.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7364-7378. (f) Boger, D. L.; Zhou, J. Biorg. Med. Chem. 1996, 4, 1597-1603 and references therein.
21. Rao, A. V. R.; Gurjar, M. K.; Reddy, L.; Rao, A. S. Chem. Rev. 1995, 95, 2135-2167.
22. D. L.; Yohannes, D. Y. J. Am. Chem. Soc. 1991, 113, 1427-1429.
23. (b) Boger, D. L.; Yohannes, D.; Zhou, J.; Patane, M. A. J. Am. Chem. Soc. 1993, 115, 3420-3430.
24. (c) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544-8556.
25. (a) Inaba, T.; Umezawa, I.; Yuasa, M.; Inoue, T.; Mihashi, S.; Itokawa, H.; Ogura, K. J. Org. Chem. 1987, 53, 2957-2958.
26. (b) Inoue, T.; Inaba, T.; Umezawa, I.; Yuasa, M.; Itokawa, H.; Ogura, K.; Komatsu, K.; Hara, H.; Hoshino, O. Chem. Pharm. Bull. 1995, 43, 1325-1335.
27. Bates, R. B.; Gin, S. L.; Hassen, M. A.; Hruby, V. J.; Janda, K. D.; Kriek, G. R.; Michaud, J. P.; Vine, D. B. Heterocycles 1984, 22, 785-790.
28. (a) Boger, D. L.; Yohannes, D. J. Org. Chem. 1988, 53, 487-499.
29. (b) Boger, D. L.; Meyers, J. B., Jr. J. Org. Chem. 1991, 56, 5385-5390.
30. Boger, D. L.; Yohannes, D. J. Org. Chem. 1991, 56, 1763-1767.
31. (a) Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1982, 23, 1281-84.
32. (b) Yamamura, S.; Nishiyama, S. In Studies in Natural Products Chemistry Atta-ur-Rahman, Ed.; Elsevier: New York, 1992; Vol. 10, pp 629-669.
33. (c) Yamamura, S.; Nishiyama, S. J. Synth. Org. Chem. Jpn. 1997, 55, 1029-1039.
34. Inoue, T.; Sazaki, T.; Takayanagi, H.; Harigara, Y.; Hoshino, O.; Hara, H.; Inaba, T. J. Org. Chem. 1996, 61, 3936-3937.
35. (a) Boger, D. L.; Zhou, J. J. Org. Chem. 1996, 61, 3938-3939.
36. (b) Boger, D. L. Zhou, J.; Borzilleri, R. M.; Nukui, S.; Castle, S. L. J. Org. Chem. 1997, 62, 2054-2069.
37. (a) For a highlight, see: Burgess, K.; Lim, D.; Martinez, C. I. Angew. Chem., Int. Ed. Engl. 1996, 35, 1077-1078.
38. (b) For a short account, see: Zhu, J. Synlett 1997, 133-144.
39. Selected examples: (a) Bois-Choussy, M.; Neuville, L.; Beugelmans, R.; Zhu, J. J. Org. Chem. 1996, 61, 9309-9322. (b) Boger, D. L. Zhou, J.; Borzilleri, R. M.; Nukui, S. Biorg. Med. Chem. Lett. 1996, 6, 1089-1092. (c) Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.; Ellman, J. A.; Rychnovsky, S. D.; Lacour, J. J. Am. Chem. Soc. 1997, 119, 3419- 3420. (d) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Li, H.; Bräse, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421- 3422. (e) Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488-6495. (f) Pearson, A. J.; Zhang, P.; Bignan, G. J. Org. Chem. 1997, 62, 4536-4538. (g) Rama Rao, A. V.; Gurjar, M. K.; Lakshmipathi, P.; Reddy, M. M.; Nagarajan, M.; Pal, S.; Sarma, B. V. N. B. S.; Tripathy, N. K. Tetrahedron Lett. 1997, 38, 7433-7436. (h) Carrington, S.; Fairlamb, A. H.; Blagbrough, I. S. J. Chem. Soc., Chem. Commun. 1998, 2335-2336. (i) Evans, D. A.; Wood, M. R.; Trotter, B. W.; Richardson, T. I.; Barrow, J. C.; Katz, J. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 2700-2704; 2704-2708. (j) Nicolaou, K. C.; Natarajan, S.; Li, H.; Jain, N. F.; Hughes, R.; Solomon, M. E.; Ramanjulu, J. M.; Boddy, C. N. C.; Takayanagi, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2708-2714; 2714-2716; 2717-2719 and references therein.
40. Selected examples: (a) Bois-Choussy, M.; Neuville, L.; Beugelmans, R.; Zhu, J. J. Org. Chem. 1996, 61, 9309-9322. (b) Boger, D. L. Zhou, J.; Borzilleri, R. M.; Nukui, S. Biorg. Med. Chem. Lett. 1996, 6, 1089-1092. (c) Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.; Ellman, J. A.; Rychnovsky, S. D.; Lacour, J. J. Am. Chem. Soc. 1997, 119, 3419- 3420. (d) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Li, H.; Bräse, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421- 3422. (e) Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488-6495. (f) Pearson, A. J.; Zhang, P.; Bignan, G. J. Org. Chem. 1997, 62, 4536-4538. (g) Rama Rao, A. V.; Gurjar, M. K.; Lakshmipathi, P.; Reddy, M. M.; Nagarajan, M.; Pal, S.; Sarma, B. V. N. B. S.; Tripathy, N. K. Tetrahedron Lett. 1997, 38, 7433-7436. (h) Carrington, S.; Fairlamb, A. H.; Blagbrough, I. S. J. Chem. Soc., Chem. Commun. 1998, 2335-2336. (i) Evans, D. A.; Wood, M. R.; Trotter, B. W.; Richardson, T. I.; Barrow, J. C.; Katz, J. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 2700-2704; 2704-2708. (j) Nicolaou, K. C.; Natarajan, S.; Li, H.; Jain, N. F.; Hughes, R.; Solomon, M. E.; Ramanjulu, J. M.; Boddy, C. N. C.; Takayanagi, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2708-2714; 2714-2716; 2717-2719 and references therein.
41. Selected examples: (a) Bois-Choussy, M.; Neuville, L.; Beugelmans, R.; Zhu, J. J. Org. Chem. 1996, 61, 9309-9322. (b) Boger, D. L. Zhou, J.; Borzilleri, R. M.; Nukui, S. Biorg. Med. Chem. Lett. 1996, 6, 1089-1092. (c) Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.; Ellman, J. A.; Rychnovsky, S. D.; Lacour, J. J. Am. Chem. Soc. 1997, 119, 3419-3420. (d) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Li, H.; Bräse, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421- 3422. (e) Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488-6495. (f) Pearson, A. J.; Zhang, P.; Bignan, G. J. Org. Chem. 1997, 62, 4536-4538. (g) Rama Rao, A. V.; Gurjar, M. K.; Lakshmipathi, P.; Reddy, M. M.; Nagarajan, M.; Pal, S.; Sarma, B. V. N. B. S.; Tripathy, N. K. Tetrahedron Lett. 1997, 38, 7433-7436. (h) Carrington, S.; Fairlamb, A. H.; Blagbrough, I. S. J. Chem. Soc., Chem. Commun. 1998, 2335-2336. (i) Evans, D. A.; Wood, M. R.; Trotter, B. W.; Richardson, T. I.; Barrow, J. C.; Katz, J. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 2700-2704; 2704-2708. (j) Nicolaou, K. C.; Natarajan, S.; Li, H.; Jain, N. F.; Hughes, R.; Solomon, M. E.; Ramanjulu, J. M.; Boddy, C. N. C.; Takayanagi, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2708-2714; 2714-2716; 2717-2719 and references therein.
42. Selected examples: (a) Bois-Choussy, M.; Neuville, L.; Beugelmans, R.; Zhu, J. J. Org. Chem. 1996, 61, 9309-9322. (b) Boger, D. L. Zhou, J.; Borzilleri, R. M.; Nukui, S. Biorg. Med. Chem. Lett. 1996, 6, 1089-1092. (c) Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.; Ellman, J. A.; Rychnovsky, S. D.; Lacour, J. J. Am. Chem. Soc. 1997, 119, 3419- 3420. (d) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Li, H.; Bräse, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421-3422. (e) Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488-6495. (f) Pearson, A. J.; Zhang, P.; Bignan, G. J. Org. Chem. 1997, 62, 4536-4538. (g) Rama Rao, A. V.; Gurjar, M. K.; Lakshmipathi, P.; Reddy, M. M.; Nagarajan, M.; Pal, S.; Sarma, B. V. N. B. S.; Tripathy, N. K. Tetrahedron Lett. 1997, 38, 7433-7436. (h) Carrington, S.; Fairlamb, A. H.; Blagbrough, I. S. J. Chem. Soc., Chem. Commun. 1998, 2335-2336. (i) Evans, D. A.; Wood, M. R.; Trotter, B. W.; Richardson, T. I.; Barrow, J. C.; Katz, J. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 2700-2704; 2704-2708. (j) Nicolaou, K. C.; Natarajan, S.; Li, H.; Jain, N. F.; Hughes, R.; Solomon, M. E.; Ramanjulu, J. M.; Boddy, C. N. C.; Takayanagi, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2708-2714; 2714-2716; 2717-2719 and references therein.
43. Selected examples: (a) Bois-Choussy, M.; Neuville, L.; Beugelmans, R.; Zhu, J. J. Org. Chem. 1996, 61, 9309-9322. (b) Boger, D. L. Zhou, J.; Borzilleri, R. M.; Nukui, S. Biorg. Med. Chem. Lett. 1996, 6, 1089-1092. (c) Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.; Ellman, J. A.; Rychnovsky, S. D.; Lacour, J. J. Am. Chem. Soc. 1997, 119, 3419- 3420. (d) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Li, H.; Bräse, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421- 3422. (e) Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488-6495. (f) Pearson, A. J.; Zhang, P.; Bignan, G. J. Org. Chem. 1997, 62, 4536-4538. (g) Rama Rao, A. V.; Gurjar, M. K.; Lakshmipathi, P.; Reddy, M. M.; Nagarajan, M.; Pal, S.; Sarma, B. V. N. B. S.; Tripathy, N. K. Tetrahedron Lett. 1997, 38, 7433-7436. (h) Carrington, S.; Fairlamb, A. H.; Blagbrough, I. S. J. Chem. Soc., Chem. Commun. 1998, 2335-2336. (i) Evans, D. A.; Wood, M. R.; Trotter, B. W.; Richardson, T. I.; Barrow, J. C.; Katz, J. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 2700-2704; 2704-2708. (j) Nicolaou, K. C.; Natarajan, S.; Li, H.; Jain, N. F.; Hughes, R.; Solomon, M. E.; Ramanjulu, J. M.; Boddy, C. N. C.; Takayanagi, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2708-2714; 2714-2716; 2717-2719 and references therein.
44. Selected examples: (a) Bois-Choussy, M.; Neuville, L.; Beugelmans, R.; Zhu, J. J. Org. Chem. 1996, 61, 9309-9322. (b) Boger, D. L. Zhou, J.; Borzilleri, R. M.; Nukui, S. Biorg. Med. Chem. Lett. 1996, 6, 1089-1092. (c) Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.; Ellman, J. A.; Rychnovsky, S. D.; Lacour, J. J. Am. Chem. Soc. 1997, 119, 3419- 3420. (d) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Li, H.; Bräse, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421- 3422. (e) Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488-6495. (f) Pearson, A. J.; Zhang, P.; Bignan, G. J. Org. Chem. 1997, 62, 4536-4538. (g) Rama Rao, A. V.; Gurjar, M. K.; Lakshmipathi, P.; Reddy, M. M.; Nagarajan, M.; Pal, S.; Sarma, B. V. N. B. S.; Tripathy, N. K. Tetrahedron Lett. 1997, 38, 7433-7436. (h) Carrington, S.; Fairlamb, A. H.; Blagbrough, I. S. J. Chem. Soc., Chem. Commun. 1998, 2335-2336. (i) Evans, D. A.; Wood, M. R.; Trotter, B. W.; Richardson, T. I.; Barrow, J. C.; Katz, J. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 2700-2704; 2704-2708. (j) Nicolaou, K. C.; Natarajan, S.; Li, H.; Jain, N. F.; Hughes, R.; Solomon, M. E.; Ramanjulu, J. M.; Boddy, C. N. C.; Takayanagi, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2708-2714; 2714-2716; 2717-2719 and references therein.
45. Selected examples: (a) Bois-Choussy, M.; Neuville, L.; Beugelmans, R.; Zhu, J. J. Org. Chem. 1996, 61, 9309-9322. (b) Boger, D. L. Zhou, J.; Borzilleri, R. M.; Nukui, S. Biorg. Med. Chem. Lett. 1996, 6, 1089-1092. (c) Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.; Ellman, J. A.; Rychnovsky, S. D.; Lacour, J. J. Am. Chem. Soc. 1997, 119, 3419- 3420. (d) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Li, H.; Bräse, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421- 3422. (e) Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488-6495. (f) Pearson, A. J.; Zhang, P.; Bignan, G. J. Org. Chem. 1997, 62, 4536-4538. (g) Rama Rao, A. V.; Gurjar, M. K.; Lakshmipathi, P.; Reddy, M. M.; Nagarajan, M.; Pal, S.; Sarma, B. V. N. B. S.; Tripathy, N. K. Tetrahedron Lett. 1997, 38, 7433-7436. (h) Carrington, S.; Fairlamb, A. H.; Blagbrough, I. S. J. Chem. Soc., Chem. Commun. 1998, 2335-2336. (i) Evans, D. A.; Wood, M. R.; Trotter, B. W.; Richardson, T. I.; Barrow, J. C.; Katz, J. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 2700-2704; 2704-2708. (j) Nicolaou, K. C.; Natarajan, S.; Li, H.; Jain, N. F.; Hughes, R.; Solomon, M. E.; Ramanjulu, J. M.; Boddy, C. N. C.; Takayanagi, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2708-2714; 2714-2716; 2717-2719 and references therein.
46. Selected examples: (a) Bois-Choussy, M.; Neuville, L.; Beugelmans, R.; Zhu, J. J. Org. Chem. 1996, 61, 9309-9322. (b) Boger, D. L. Zhou, J.; Borzilleri, R. M.; Nukui, S. Biorg. Med. Chem. Lett. 1996, 6, 1089-1092. (c) Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.; Ellman, J. A.; Rychnovsky, S. D.; Lacour, J. J. Am. Chem. Soc. 1997, 119, 3419- 3420. (d) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Li, H.; Bräse, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421- 3422. (e) Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488-6495. (f) Pearson, A. J.; Zhang, P.; Bignan, G. J. Org. Chem. 1997, 62, 4536-4538. (g) Rama Rao, A. V.; Gurjar, M. K.; Lakshmipathi, P.; Reddy, M. M.; Nagarajan, M.; Pal, S.; Sarma, B. V. N. B. S.; Tripathy, N. K. Tetrahedron Lett. 1997, 38, 7433-7436. (h) Carrington, S.; Fairlamb, A. H.; Blagbrough, I. S. J. Chem. Soc., Chem. Commun. 1998, 2335-2336. (i) Evans, D. A.; Wood, M. R.; Trotter, B. W.; Richardson, T. I.; Barrow, J. C.; Katz, J. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 2700-2704; 2704-2708. (j) Nicolaou, K. C.; Natarajan, S.; Li, H.; Jain, N. F.; Hughes, R.; Solomon, M. E.; Ramanjulu, J. M.; Boddy, C. N. C.; Takayanagi, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2708-2714; 2714-2716; 2717-2719 and references therein.
47. Selected examples: (a) Bois-Choussy, M.; Neuville, L.; Beugelmans, R.; Zhu, J. J. Org. Chem. 1996, 61, 9309-9322. (b) Boger, D. L. Zhou, J.; Borzilleri, R. M.; Nukui, S. Biorg. Med. Chem. Lett. 1996, 6, 1089-1092. (c) Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.; Ellman, J. A.; Rychnovsky, S. D.; Lacour, J. J. Am. Chem. Soc. 1997, 119, 3419- 3420. (d) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Li, H.; Bräse, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421- 3422. (e) Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488-6495. (f) Pearson, A. J.; Zhang, P.; Bignan, G. J. Org. Chem. 1997, 62, 4536-4538. (g) Rama Rao, A. V.; Gurjar, M. K.; Lakshmipathi, P.; Reddy, M. M.; Nagarajan, M.; Pal, S.; Sarma, B. V. N. B. S.; Tripathy, N. K. Tetrahedron Lett. 1997, 38, 7433-7436. (h) Carrington, S.; Fairlamb, A. H.; Blagbrough, I. S. J. Chem. Soc., Chem. Commun. 1998, 2335-2336. (i) Evans, D. A.; Wood, M. R.; Trotter, B. W.; Richardson, T. I.; Barrow, J. C.; Katz, J. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 2700-2704; 2704-2708. (j) Nicolaou, K. C.; Natarajan, S.; Li, H.; Jain, N. F.; Hughes, R.; Solomon, M. E.; Ramanjulu, J. M.; Boddy, C. N. C.; Takayanagi, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2708-2714; 2714-2716; 2717-2719 and references therein.
48. Selected examples: (a) Bois-Choussy, M.; Neuville, L.; Beugelmans, R.; Zhu, J. J. Org. Chem. 1996, 61, 9309-9322. (b) Boger, D. L. Zhou, J.; Borzilleri, R. M.; Nukui, S. Biorg. Med. Chem. Lett. 1996, 6, 1089-1092. (c) Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.; Ellman, J. A.; Rychnovsky, S. D.; Lacour, J. J. Am. Chem. Soc. 1997, 119, 3419- 3420. (d) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Li, H.; Bräse, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421- 3422. (e) Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488-6495. (f) Pearson, A. J.; Zhang, P.; Bignan, G. J. Org. Chem. 1997, 62, 4536-4538. (g) Rama Rao, A. V.; Gurjar, M. K.; Lakshmipathi, P.; Reddy, M. M.; Nagarajan, M.; Pal, S.; Sarma, B. V. N. B. S.; Tripathy, N. K. Tetrahedron Lett. 1997, 38, 7433-7436. (h) Carrington, S.; Fairlamb, A. H.; Blagbrough, I. S. J. Chem. Soc., Chem. Commun. 1998, 2335-2336. (i) Evans, D. A.; Wood, M. R.; Trotter, B. W.; Richardson, T. I.; Barrow, J. C.; Katz, J. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 2700-2704; 2704-2708. (j) Nicolaou, K. C.; Natarajan, S.; Li, H.; Jain, N. F.; Hughes, R.; Solomon, M. E.; Ramanjulu, J. M.; Boddy, C. N. C.; Takayanagi, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2708-2714; 2714-2716; 2717-2719 and references therein.
49. (a) Zhu, J.; Laïb, T.; Beugelmans, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2517-2519.
50. (b) Laïb, T.; Zhu, J. Tetrahedron Lett. 1999, 40, 83-86.
51. (a) Beugelmans, R.; Bigot, A.; Zhu, J. J. Org. Chem. 1996, 61, 771-774. In this paper, two epimers were erronously assigned as two atropisomers:
52. (b) Bigot, A.; Beugelmans, R.; Zhu, J. Tetrahedron 1997, 53, 10753-10764.
53. Boger, D. L.; Borzilleri, R. M. Biorg. Med. Chem. Lett. 1995, 5, 1187-1190.
54. (b) Boger, D. L.; Borzilleri, R. M. Nukui, S. Biorg. Med. Chem. Lett. 1995, 5, 3091-94.
55. (c) Boger, D. L.; Borzilleri, R. M. Nukui, S. Biorg. Med. Chem. Lett. 1996, 6, 1089-1092.
56. McDermott, J. R.; Benoiton, N. L. Can. J. Chem. 1973, 51, 2555-2561.
57. (a) Henning, R.; Lehr, F.; Seebach, D. Helv. Chim. Acta 1976, 59, 2213-2217.
58. (b) Seebach, D.; Henning, R.; Lehr, F.; Gonnermann, J. Tetrahedron Lett. 1977, 1161-1164.
59. (c) Seebach, D.; Henning, R.; Lehr, F. Angew. Chem., Int. Ed. Engl. 1978, 17, 458-459.
60. (d) Yamada, K.; Tanaka, S.; Kohmoto, S.; Yamamoto, M. J. Chem. Soc., Chem. Commun. 1989, 110-111.
61. (e) Bergman, J.; Sand, P.; Tilstam, U. Tetrahedron Lett. 1983, 24, 3665-3668.
62. During cyclization, a phenolate anion is formed on the residue at C-9, which further reduces the kinetic acidity of 9-H. We thank one of reviewers for this insightful consideration.
63. Part of this work was published as a preliminary communication; see: Bigot, A.; Zhu, J. Tetrahedron Lett. 1998, 39, 551-554.
64. (a) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1997, 62, 1553-1555.
65. (b) Boger, D. L.; Yohannes, D. J. Org. Chem. 1987, 52, 5283-5286 and references therein.
66. Konda, M.; Takayuki, S.; Yamada, S.-I. Chem. Pharm. Bull. 1975, 23, 1063-76.
67. (a) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011-4030.
68. (b) Evans, D. A.; Evrard, D. A.; Rychnovsky, S. D.; Früh, T.; Whittingham, W. G.; Devries, K. M. Tetrahedron Lett. 1992, 33, 1189-1192.
69. Pearson, A. J.; Zhang, P.; Lee, K. J. Org. Chem. 1996, 61, 6581-6586.
70. Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757-6761.
71. Vergne, C.; Bois-Choussy, M.; Ouazzani, J.; Beugelmans, R.; Zhu, J. Tetrahedron Asymmetry 1997, 8, 391-398.
72. Sala, T.; Sargent, M. V. J. Chem. Soc., Perkin Trans. 1 1979, 2593-2598.
73. (a) Vergne, C.; Bois-Choussy, M.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1997, 38, 1403-1406.
74. (b) Bois-Choussy, M.; Vergne, C.; Neuville, L.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1997, 38, 5795-5798.
75. The configuration (P or M) of the atropisomer was determined by viewing the atropisomer as helix. "For this designation, only the ligands of highest priority in front and in the back of the framework are considered. If the turn from the priority front ligand to the priority rear ligand is clockwise, the configuration is P, if counterclockwise it is M". See: Eliel, E. L.; Willen, S. H. Stereochemistry of Organic Compounds; John Wiley & Sons Inc.: New York, 1994; Chapter 14.
76. Rhee, E. S.; Shine, H. J. J. Am. Chem. Soc. 1986, 108, 1000-1006.
77. (a) Doyle, M. P.; Dellaria, J. F.; Siegfried, Jr. B.; Bishop, S. W. J. Org. Chem. 1977, 42, 3494-3498.
78. (b) Islas-Gonzalez, G.; Zhu, J. J. Org. Chem. 1997, 62, 7544-7545.
79. (a) Doyle, M. P.; Bryker, W. J. J. Org. Chem. 1979, 44, 1572-1574.
80. (b) Wassmundt, F. W.; Kiesman, W. F. J. Org. Chem. 1995, 60, 1713-1719.
81. (a) Andrus, M. B.; Li, W. K.; Keyes, R. F. Tetrahedron Lett. 1998, 39, 5465-5468.
82. (b) Hargreaves, M. K.; Pritchard, J. G.; Dave, H. R. Chem. Rev. 1970, 70, 439-469.
83. A very similar product was obtained in Boger's synthesis of piperazinomycin; see: Boger, D. L.; Zhou, J. J. Am. Chem. Soc. 1993, 115, 11426-11433 and ref 9b.
84. (a) Truce, W. E.; Kreider, E. M.; Brand, W. W. The Smiles and related rearrangements of aromatic systems. Organic Reactions; John Wiley & Sons Inc.: New York, 1970; Vol. 18, pp 99-215.
85. (b) Borchardt, A.; Still, W. C. Synlett 1995, 539-540 and references therein.
86. Beugelmans, R.; Singh, G. P.; Bois-Choussy, M.; Chastanet, J.; Zhu, J. J. Org. Chem. 1994, 59, 5535-5542.
87. While it was a symmetric dimer, the regiochemistry was not determined rigorously.
88. Wiberg, K. B. Angew. Chem., Int. Ed. Engl. 1986, 25, 312-322.
89. Humphrey, J. M.; Chamberlin, A. R. Chem. Rev. 1997, 97, 2243-2266.
90. For recent books and reviews, see: (a) Terrier, F. Nucleophilic Aromatic Displacement: The Role of the Nitro Group; VCH: New York, 1991; Chapter 1. (b) Paradisi, C. Arene Substitution via Nucleophilic Addition to Electron Deficient Arenes. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 4, pp 423-450. (c) Vlasov, V. M. J. Fluorine Chem. 1993, 61, 193-216.
91. For recent books and reviews, see: (a) Terrier, F. Nucleophilic Aromatic Displacement: The Role of the Nitro Group; VCH: New York, 1991; Chapter 1. (b) Paradisi, C. Arene Substitution via Nucleophilic Addition to Electron Deficient Arenes. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 4, pp 423-450. (c) Vlasov, V. M. J. Fluorine Chem. 1993, 61, 193-216.
92. For recent books and reviews, see: (a) Terrier, F. Nucleophilic Aromatic Displacement: The Role of the Nitro Group; VCH: New York, 1991; Chapter 1. (b) Paradisi, C. Arene Substitution via Nucleophilic Addition to Electron Deficient Arenes. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 4, pp 423-450. (c) Vlasov, V. M. J. Fluorine Chem. 1993, 61, 193-216.
93. Chang, G.; Guida, W. C.; Still, W. C. J. Am. Chem. Soc. 1989, 111, 4379-4386.
94. Ponder, J. W.; Richards, F. M. J. Comput. Chem. 1987, 8, 1016-1024.
95. Mohamadi, F.; Richards, N. J. G.; Guida, W. C.; Liskamp, R.; Lipton, M. C.; Caufield, M.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
96. Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127-8134.
97. (a) Menger, F. M. Acc. Chem. Res. 1986, 18, 128-134.
98. (b) Mandolini, L. Bull. Soc. Chim. Fr. 1988, 173-176.
99. (c) Bruice, T. C.; Lightstone, F. C. Acc. Chem. Res. 1999, 32, 127-136.
100. As pointed out by one of reviewers, we agree that the comparison of energies between 41 and 56 may not be relevant in the present case since compound 56 has never been isolated.