Practical Asymmetric Synthesis of (S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione, a Key Intermediate for the Synthesis of Irinotecan and Other Camptothecin Analogs

Journal of Organic Chemistry

Volumn 62, Issue 19, 1997, Pages 6588-6597

  Henegar, Kevin E ^a   Ashford, Scott W ^a   Baughman, Ted A ^a   Sih, John C ^a   Gu, Rui Lin ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPTOTHECIN DERIVATIVE; DIPYRONE; INDOLIZINE DERIVATIVE; IRINOTECAN; PYRIDINE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL REACTION; COLORECTAL CANCER; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; OXIDATION; RACEMIC MIXTURE; STEREOCHEMISTRY;

EID: 0030845935     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970173f     Document Type: Article

References (64)

1. Sawada, S.; Okajima, S.; Aiyama, R.; Nokata, K.; Furuta, T.; Yokokura, T.; Sugino, E.; Yamaguchi, K.; Miyasaka, T. Chem. Pharm. Bull. 1991, 39, 1446-1454.
2. Wall, M. E.; Wani, M. C.; Cook, C. E.; Palmer, K. H.; McPhail, A. T.; Sim, G. A. J. Am. Chem. Soc. 1966, 88, 3888-3890.
3. (a) Kingsbury, W. D.; Boehm, J. C.; Jakas, D. R.; Holden, K. G.; Hecht, S. M.; Gallagher, G.; Caranfa, M. J.; McCabe, F. L.; Faucette, L. F.; Johnson, R. K.; Hertzberg, R. P. J. Med. Chem. 1991, 34, 98-107.
4. (b) Wall, M. E.; Wani, M. C.; Nicholas, A. W.; Manikumar, G.; Tele, C.; Moore, L.; Truesdale, A.; Leitner, P.; Besterman, J. M. J. Med. Chem. 1993, 36, 2689-2700.
5. (c) Luzzio, M. J.; Besterman, J. M.; Emerson, D. L.; Evans, M. G.; Lackey, K.; Leitner, P. L.; McIntyre, 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, 395-401.
6. Camptothecins: New Anticancer Agents; Potsmeil, M., Pinedo, H., Eds.; CRC Press: Boca Raton, 1995.
7. (a) Hutchinson, C. R. Tetrahedron 1981, 37, 1047-1065.
8. (b) Schultz, A. G. Chem. Rev. 1973, 73, 385-405.
9. (c) Shamma, M.; St. Georgiev, V. J. Pharm. Sci. 1974, 63, 163-183.
10. Leading references: (a) Wani, M. C.; Nicholas, A. W.; Wall, M. E. J. Med. Chem. 1987, 30, 2317-2319. (b) Terasawa, H.; Sugímorí, M.; Ejima, A.; Tagawa, H. Chem. Pharm. Bull. 1989, 37, 3382-3385. Ejima, A.; Terasawa, H.; Sugimori, M.; Tagawa, H. J. Chem. Soc., Perkin Trans. 1 1990, 27-31. (d) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863-5864. (e) Comins, D. L.; Baevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971-10972. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611-617. (g) Comins, D. L.; Hong.; H., Saha, J. K.; Jianhua G. J. Org. Chem. 1994, 59, 5120-5121. (h) Comins, D. L.; Hong.; H., Jianhua, G. Tetrahedron Lett. 1994, 35, 5331-5334. (i) Fang, F. G.; Xie, S.; Lowery, M. W. J. Org. Chem. 1994, 59, 6142-6143. (j) Curran, D. P.; Ko, S.-B.; Josien, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2683-2684. (k) Comins, D. L.; Saha, J. K. Tetrahedron Lett. 1995, 36, 7995-7998. Fortunak, J. M. D.; Kitteringham, J.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5683-5686. (m) Ciufolini, M. A.; Roschanger, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1692-1694.
11. Leading references: (a) Wani, M. C.; Nicholas, A. W.; Wall, M. E. J. Med. Chem. 1987, 30, 2317-2319. (b) Terasawa, H.; Sugímorí, M.; Ejima, A.; Tagawa, H. Chem. Pharm. Bull. 1989, 37, 3382-3385. Ejima, A.; Terasawa, H.; Sugimori, M.; Tagawa, H. J. Chem. Soc., Perkin Trans. 1 1990, 27-31. (d) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863-5864. (e) Comins, D. L.; Baevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971-10972. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611-617. (g) Comins, D. L.; Hong.; H., Saha, J. K.; Jianhua G. J. Org. Chem. 1994, 59, 5120-5121. (h) Comins, D. L.; Hong.; H., Jianhua, G. Tetrahedron Lett. 1994, 35, 5331-5334. (i) Fang, F. G.; Xie, S.; Lowery, M. W. J. Org. Chem. 1994, 59, 6142-6143. (j) Curran, D. P.; Ko, S.-B.; Josien, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2683-2684. (k) Comins, D. L.; Saha, J. K. Tetrahedron Lett. 1995, 36, 7995-7998. Fortunak, J. M. D.; Kitteringham, J.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5683-5686. (m) Ciufolini, M. A.; Roschanger, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1692-1694.
12. Leading references: (a) Wani, M. C.; Nicholas, A. W.; Wall, M. E. J. Med. Chem. 1987, 30, 2317-2319. (b) Terasawa, H.; Sugímorí, M.; Ejima, A.; Tagawa, H. Chem. Pharm. Bull. 1989, 37, 3382-3385. Ejima, A.; Terasawa, H.; Sugimori, M.; Tagawa, H. J. Chem. Soc., Perkin Trans. 1 1990, 27-31. (d) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863-5864. (e) Comins, D. L.; Baevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971-10972. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611-617. (g) Comins, D. L.; Hong.; H., Saha, J. K.; Jianhua G. J. Org. Chem. 1994, 59, 5120-5121. (h) Comins, D. L.; Hong.; H., Jianhua, G. Tetrahedron Lett. 1994, 35, 5331-5334. (i) Fang, F. G.; Xie, S.; Lowery, M. W. J. Org. Chem. 1994, 59, 6142-6143. (j) Curran, D. P.; Ko, S.-B.; Josien, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2683-2684. (k) Comins, D. L.; Saha, J. K. Tetrahedron Lett. 1995, 36, 7995-7998. Fortunak, J. M. D.; Kitteringham, J.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5683-5686. (m) Ciufolini, M. A.; Roschanger, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1692-1694.
13. Leading references: (a) Wani, M. C.; Nicholas, A. W.; Wall, M. E. J. Med. Chem. 1987, 30, 2317-2319. (b) Terasawa, H.; Sugímorí, M.; Ejima, A.; Tagawa, H. Chem. Pharm. Bull. 1989, 37, 3382-3385. Ejima, A.; Terasawa, H.; Sugimori, M.; Tagawa, H. J. Chem. Soc., Perkin Trans. 1 1990, 27-31. (d) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863-5864. (e) Comins, D. L.; Baevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971-10972. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611-617. (g) Comins, D. L.; Hong.; H., Saha, J. K.; Jianhua G. J. Org. Chem. 1994, 59, 5120-5121. (h) Comins, D. L.; Hong.; H., Jianhua, G. Tetrahedron Lett. 1994, 35, 5331-5334. (i) Fang, F. G.; Xie, S.; Lowery, M. W. J. Org. Chem. 1994, 59, 6142-6143. (j) Curran, D. P.; Ko, S.-B.; Josien, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2683-2684. (k) Comins, D. L.; Saha, J. K. Tetrahedron Lett. 1995, 36, 7995-7998. Fortunak, J. M. D.; Kitteringham, J.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5683-5686. (m) Ciufolini, M. A.; Roschanger, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1692-1694.
14. Leading references: (a) Wani, M. C.; Nicholas, A. W.; Wall, M. E. J. Med. Chem. 1987, 30, 2317-2319. (b) Terasawa, H.; Sugímorí, M.; Ejima, A.; Tagawa, H. Chem. Pharm. Bull. 1989, 37, 3382-3385. Ejima, A.; Terasawa, H.; Sugimori, M.; Tagawa, H. J. Chem. Soc., Perkin Trans. 1 1990, 27-31. (d) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863-5864. (e) Comins, D. L.; Baevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971-10972. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611-617. (g) Comins, D. L.; Hong.; H., Saha, J. K.; Jianhua G. J. Org. Chem. 1994, 59, 5120-5121. (h) Comins, D. L.; Hong.; H., Jianhua, G. Tetrahedron Lett. 1994, 35, 5331-5334. (i) Fang, F. G.; Xie, S.; Lowery, M. W. J. Org. Chem. 1994, 59, 6142-6143. (j) Curran, D. P.; Ko, S.-B.; Josien, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2683-2684. (k) Comins, D. L.; Saha, J. K. Tetrahedron Lett. 1995, 36, 7995-7998. Fortunak, J. M. D.; Kitteringham, J.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5683-5686. (m) Ciufolini, M. A.; Roschanger, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1692-1694.
15. Leading references: (a) Wani, M. C.; Nicholas, A. W.; Wall, M. E. J. Med. Chem. 1987, 30, 2317-2319. (b) Terasawa, H.; Sugímorí, M.; Ejima, A.; Tagawa, H. Chem. Pharm. Bull. 1989, 37, 3382-3385. Ejima, A.; Terasawa, H.; Sugimori, M.; Tagawa, H. J. Chem. Soc., Perkin Trans. 1 1990, 27-31. (d) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863-5864. (e) Comins, D. L.; Baevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971-10972. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611-617. (g) Comins, D. L.; Hong.; H., Saha, J. K.; Jianhua G. J. Org. Chem. 1994, 59, 5120-5121. (h) Comins, D. L.; Hong.; H., Jianhua, G. Tetrahedron Lett. 1994, 35, 5331-5334. (i) Fang, F. G.; Xie, S.; Lowery, M. W. J. Org. Chem. 1994, 59, 6142-6143. (j) Curran, D. P.; Ko, S.-B.; Josien, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2683-2684. (k) Comins, D. L.; Saha, J. K. Tetrahedron Lett. 1995, 36, 7995-7998. Fortunak, J. M. D.; Kitteringham, J.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5683-5686. (m) Ciufolini, M. A.; Roschanger, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1692-1694.
16. Leading references: (a) Wani, M. C.; Nicholas, A. W.; Wall, M. E. J. Med. Chem. 1987, 30, 2317-2319. (b) Terasawa, H.; Sugímorí, M.; Ejima, A.; Tagawa, H. Chem. Pharm. Bull. 1989, 37, 3382-3385. Ejima, A.; Terasawa, H.; Sugimori, M.; Tagawa, H. J. Chem. Soc., Perkin Trans. 1 1990, 27-31. (d) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863-5864. (e) Comins, D. L.; Baevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971-10972. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611-617. (g) Comins, D. L.; Hong.; H., Saha, J. K.; Jianhua G. J. Org. Chem. 1994, 59, 5120-5121. (h) Comins, D. L.; Hong.; H., Jianhua, G. Tetrahedron Lett. 1994, 35, 5331-5334. (i) Fang, F. G.; Xie, S.; Lowery, M. W. J. Org. Chem. 1994, 59, 6142-6143. (j) Curran, D. P.; Ko, S.-B.; Josien, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2683-2684. (k) Comins, D. L.; Saha, J. K. Tetrahedron Lett. 1995, 36, 7995-7998. Fortunak, J. M. D.; Kitteringham, J.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5683-5686. (m) Ciufolini, M. A.; Roschanger, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1692-1694.
17. Leading references: (a) Wani, M. C.; Nicholas, A. W.; Wall, M. E. J. Med. Chem. 1987, 30, 2317-2319. (b) Terasawa, H.; Sugímorí, M.; Ejima, A.; Tagawa, H. Chem. Pharm. Bull. 1989, 37, 3382-3385. Ejima, A.; Terasawa, H.; Sugimori, M.; Tagawa, H. J. Chem. Soc., Perkin Trans. 1 1990, 27-31. (d) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863-5864. (e) Comins, D. L.; Baevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971-10972. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611-617. (g) Comins, D. L.; Hong.; H., Saha, J. K.; Jianhua G. J. Org. Chem. 1994, 59, 5120-5121. (h) Comins, D. L.; Hong.; H., Jianhua, G. Tetrahedron Lett. 1994, 35, 5331-5334. (i) Fang, F. G.; Xie, S.; Lowery, M. W. J. Org. Chem. 1994, 59, 6142-6143. (j) Curran, D. P.; Ko, S.-B.; Josien, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2683-2684. (k) Comins, D. L.; Saha, J. K. Tetrahedron Lett. 1995, 36, 7995-7998. Fortunak, J. M. D.; Kitteringham, J.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5683-5686. (m) Ciufolini, M. A.; Roschanger, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1692-1694.
18. Leading references: (a) Wani, M. C.; Nicholas, A. W.; Wall, M. E. J. Med. Chem. 1987, 30, 2317-2319. (b) Terasawa, H.; Sugímorí, M.; Ejima, A.; Tagawa, H. Chem. Pharm. Bull. 1989, 37, 3382-3385. Ejima, A.; Terasawa, H.; Sugimori, M.; Tagawa, H. J. Chem. Soc., Perkin Trans. 1 1990, 27-31. (d) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863-5864. (e) Comins, D. L.; Baevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971-10972. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611-617. (g) Comins, D. L.; Hong.; H., Saha, J. K.; Jianhua G. J. Org. Chem. 1994, 59, 5120-5121. (h) Comins, D. L.; Hong.; H., Jianhua, G. Tetrahedron Lett. 1994, 35, 5331-5334. (i) Fang, F. G.; Xie, S.; Lowery, M. W. J. Org. Chem. 1994, 59, 6142-6143. (j) Curran, D. P.; Ko, S.-B.; Josien, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2683-2684. (k) Comins, D. L.; Saha, J. K. Tetrahedron Lett. 1995, 36, 7995-7998. Fortunak, J. M. D.; Kitteringham, J.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5683-5686. (m) Ciufolini, M. A.; Roschanger, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1692-1694.
19. Leading references: (a) Wani, M. C.; Nicholas, A. W.; Wall, M. E. J. Med. Chem. 1987, 30, 2317-2319. (b) Terasawa, H.; Sugímorí, M.; Ejima, A.; Tagawa, H. Chem. Pharm. Bull. 1989, 37, 3382-3385. Ejima, A.; Terasawa, H.; Sugimori, M.; Tagawa, H. J. Chem. Soc., Perkin Trans. 1 1990, 27-31. (d) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863-5864. (e) Comins, D. L.; Baevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971-10972. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611-617. (g) Comins, D. L.; Hong.; H., Saha, J. K.; Jianhua G. J. Org. Chem. 1994, 59, 5120-5121. (h) Comins, D. L.; Hong.; H., Jianhua, G. Tetrahedron Lett. 1994, 35, 5331-5334. (i) Fang, F. G.; Xie, S.; Lowery, M. W. J. Org. Chem. 1994, 59, 6142-6143. (j) Curran, D. P.; Ko, S.-B.; Josien, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2683-2684. (k) Comins, D. L.; Saha, J. K. Tetrahedron Lett. 1995, 36, 7995-7998. Fortunak, J. M. D.; Kitteringham, J.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5683-5686. (m) Ciufolini, M. A.; Roschanger, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1692-1694.
20. Leading references: (a) Wani, M. C.; Nicholas, A. W.; Wall, M. E. J. Med. Chem. 1987, 30, 2317-2319. (b) Terasawa, H.; Sugímorí, M.; Ejima, A.; Tagawa, H. Chem. Pharm. Bull. 1989, 37, 3382-3385. Ejima, A.; Terasawa, H.; Sugimori, M.; Tagawa, H. J. Chem. Soc., Perkin Trans. 1 1990, 27-31. (d) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863-5864. (e) Comins, D. L.; Baevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971-10972. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611-617. (g) Comins, D. L.; Hong.; H., Saha, J. K.; Jianhua G. J. Org. Chem. 1994, 59, 5120-5121. (h) Comins, D. L.; Hong.; H., Jianhua, G. Tetrahedron Lett. 1994, 35, 5331-5334. (i) Fang, F. G.; Xie, S.; Lowery, M. W. J. Org. Chem. 1994, 59, 6142-6143. (j) Curran, D. P.; Ko, S.-B.; Josien, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2683-2684. (k) Comins, D. L.; Saha, J. K. Tetrahedron Lett. 1995, 36, 7995-7998. Fortunak, J. M. D.; Kitteringham, J.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5683-5686. (m) Ciufolini, M. A.; Roschanger, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1692-1694.
21. Leading references: (a) Wani, M. C.; Nicholas, A. W.; Wall, M. E. J. Med. Chem. 1987, 30, 2317-2319. (b) Terasawa, H.; Sugímorí, M.; Ejima, A.; Tagawa, H. Chem. Pharm. Bull. 1989, 37, 3382-3385. Ejima, A.; Terasawa, H.; Sugimori, M.; Tagawa, H. J. Chem. Soc., Perkin Trans. 1 1990, 27-31. (d) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863-5864. (e) Comins, D. L.; Baevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971-10972. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611-617. (g) Comins, D. L.; Hong.; H., Saha, J. K.; Jianhua G. J. Org. Chem. 1994, 59, 5120-5121. (h) Comins, D. L.; Hong.; H., Jianhua, G. Tetrahedron Lett. 1994, 35, 5331-5334. (i) Fang, F. G.; Xie, S.; Lowery, M. W. J. Org. Chem. 1994, 59, 6142-6143. (j) Curran, D. P.; Ko, S.-B.; Josien, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2683-2684. (k) Comins, D. L.; Saha, J. K. Tetrahedron Lett. 1995, 36, 7995-7998. Fortunak, J. M. D.; Kitteringham, J.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5683-5686. (m) Ciufolini, M. A.; Roschanger, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1692-1694.
22. Leading references: (a) Wani, M. C.; Nicholas, A. W.; Wall, M. E. J. Med. Chem. 1987, 30, 2317-2319. (b) Terasawa, H.; Sugímorí, M.; Ejima, A.; Tagawa, H. Chem. Pharm. Bull. 1989, 37, 3382-3385. Ejima, A.; Terasawa, H.; Sugimori, M.; Tagawa, H. J. Chem. Soc., Perkin Trans. 1 1990, 27-31. (d) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863-5864. (e) Comins, D. L.; Baevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971-10972. (f) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611-617. (g) Comins, D. L.; Hong.; H., Saha, J. K.; Jianhua G. J. Org. Chem. 1994, 59, 5120-5121. (h) Comins, D. L.; Hong.; H., Jianhua, G. Tetrahedron Lett. 1994, 35, 5331-5334. (i) Fang, F. G.; Xie, S.; Lowery, M. W. J. Org. Chem. 1994, 59, 6142-6143. (j) Curran, D. P.; Ko, S.-B.; Josien, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2683-2684. (k) Comins, D. L.; Saha, J. K. Tetrahedron Lett. 1995, 36, 7995-7998. Fortunak, J. M. D.; Kitteringham, J.; Mastrocola, A. R.; Mellinger, M.; Sisti, N. J.; Wood, J. L.; Zhuang, Z.-P. Tetrahedron Lett. 1996, 37, 5683-5686. (m) Ciufolini, M. A.; Roschanger, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1692-1694.
23. Cheng, C.-C.; Yan, S.-J. Organic Reactions; J. Wiley: New York, 1982; vol. 28, pp 37-202.
24. (a) Wani, M. C.; Ronman, P. E.; Lindley, J. T.; Wall, M. E. J. Med. Chem. 1980, 23, 554-560.
25. (b) Wani, M. C.; Nicholas, A. W.; Natschke, S. M.; Wall, M. E. J. Med. Chem. 1986, 29, 1553-1555.
26. (a) Chem. Abstr. 1976, 84, 122100.
27. (b) Sci. Sin. [Engl. Ed.] 1978, 21, 87.
28. 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, 1245-1248.
29. Citrazinic acid was purchased from Yorkshire Chemical for $60/kg.
30. Schroetter, E.; Schick, H.; Niedrich, H.; Oehme, P.; Piesche, L. German (East) Pat. DD 154,538; Chem. Abstr. 1982, 97, 216024.
31. (a) Baizer, M. E.; Dub, M.; Gister, S.; Steinberg, N. G. J. Am. Pharm. Soc. 1956, 45, 478-480.
32. (b) Levelt, W. H.; Wibalt, J. P. Rec. Trav. Chem. 1929, 44, 466.
33. Chan, T. H.; Brook, M. A.; Chaly, T. Synthesis 1983, 203-205.
34. For related selective displacements of halopyridines: (a) Testaferri, L.; Tieco, M.; Tingoli, M.; Bartoli, D.; Massoli, A. Tetrahedron 1985, 41, 1371-1384. (b) Murata, N.; Sugihara, T.; Kondo, Y.; Sakamoto, T. Synlett 1997, 298-300.
35. For related selective displacements of halopyridines: (a) Testaferri, L.; Tieco, M.; Tingoli, M.; Bartoli, D.; Massoli, A. Tetrahedron 1985, 41, 1371-1384. (b) Murata, N.; Sugihara, T.; Kondo, Y.; Sakamoto, T. Synlett 1997, 298-300.
36. Snieckus, V. Chem. Rev. 1990, 90, 879-933.
37. (a) Winkle, M. R.; Ronald, R. C. J. Org. Chem. 1982, 47, 2101-2108.
38. (b) Coming, D. L.; LaMunyon, D. H. Tetrahedron Lett. 1988, 29, 773-776.
39. (c) Trecourt, F.; Mallet, M.; Marsais, F.; Queguiner, G. J. Org. Chem. 1988, 53, 1367-1371.
40. (d) Comins, D. L.; Killpack, M. O. J. Org. Chem. 1990, 55, 69-73.
41. (e) Hong., H.; Comins, D. L. J. Org. Chem. 1996, 61, 391-392.
42. Ashby, E. C.; Lin, J. J. J. Org Chem. 1978, 43, 1263-1265.
43. (a) Isobe, K.; Kawaguchi, S. Heterocycles 1981, 16, 1603-1612.
44. (b) Ishikura, M.; Kamada, M.; Terashima, M. Synthesis 1984, 936-938.
45. (c) Isobe, K.; Nanjo, K.; Nakamura, Y.; Kawaguchi, S. Bull. Chem. Soc. Jpn. 1986, 59, 2141-2149.
46. (d) Sato, N.; Hayakawa, A.; Takeuchi, R. J. Heterocycl. Chem. 1990, 27, 503-506.
47. Uijttewaal, A. P.; Jonkers, F. L.; van der Gen, A. Tetrahedron Lett. 1975, 1439-1442.
48. 2-phthal required 48 h to go to > 90% completion and gave diol product with an ee of 68% (Henegar, K. E.; Baughman, T. A., unpublished results). In view of our requirement for an ee > 99% for the final product and time constraints, optimization of the asymmetric dihydroxylation was deferred in favor of a lipase resolution of the racemic diol to establish the enantiomeric purity. Chemical equation presented.
49. (a) Crispino, G. A.; Jeong, K.-S.; Kolb, H. C.; Wang, Z.-M.; Xu, D.; Sharpless, K. B. J. Org. Chem. 1993, 58, 3785-3786, and references cited in this paper.
50. (b) Crispino, G. A.; Makita, A.; Wang, Z.-M.; Sharpless, K. B. Tetrahedron Lett. 1994, 35, 543-546.
51. Van Rheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 1973-1976.
52. Assignment of the absolute stereochemistry of this intermediate was done by conversion into 1 and comparison of the sign of the specific rotation with published values from material of known absolute stereochemistry. Determination of enantiomeric purity of the diol 16 and of later intermediates was made by chiral HPLC analysis.
53. Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294-7299.
54. (a) Hanessian, S.; Bargiotti, A.; LaRue, M. Tetrahedron Lett. 1978, 737-740.
55. (b) Eastwood, F. W.; Harrington, K. J.; Josan, J. S.; Pura, J. L. Tetrahedron Lett. 1970, 5223-5224.
56. Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559-2562. TEMPO and 4-acetoxy-TEMPO were used interchangeably for the oxidations of 17 and 22.
57. (a) Olah, G. A.; Narang, S. C.; Gupta, B. G. B.; Malhotra, R. J. Org. Chem. 1979, 44, 1247-1251.
58. (b) Jung, M. E.; Lyster, M. A. J. Org. Chem. 1977, 42, 3761-3763.
59. (c) Monta, T.; Okamoto, Y.; Sakurai, H. J. Chem. Soc., Chem. Commun. 1978, 874-875.
60. Giovannini, E.; Rosales, J.; de Souza, B. Helv. Chem. Acta 1971, 54, 2111-2113. Material used here was prepared from 2-nitro-5-hydroxybenzaldehyde (five steps) or from p-anisidine (one step) (Baughman, T. A.; Hewitt, B. D.; Henegar, K. E., unpublished results).
61. Giovannini, E.; Rosales, J.; de Souza, B. Helv. Chem. Acta 1971, 54, 2111-2113. Material used here was prepared from 2-nitro-5-hydroxybenzaldehyde (five steps) or from p-anisidine (one step) (Baughman, T. A.; Hewitt, B. D.; Henegar, K. E., unpublished results).
62. Tagawa, H.; Terasawa, H.; Ejima, A. Eur. Pat. Appl. 114231, 1986.
63. 3).
64. Tagawa, H.; Terasawa, E. U.S. Pat. 4,778,891.