Ni(II)/Cr(II)-mediated coupling reaction: Beneficial effects of 4-tert-Butylpyridine as an additive and development of new and improved workup procedures

Tetrahedron Letters

Volumn 38, Issue 36, 1997, Pages 6355-6358

  Stamos, Dean P ^a   Sheng, X Christopher ^a   Chen, Sean S ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TAXANE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0030754285     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01462-7     Document Type: Article

References (23)

1. (a) Jin, H.; Uenishi, J-I.; Christ, W. J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644-5646.
2. (b) Takai, K.; Tagashira, M.; Kuroda, T.; Oshima, K.; Utimoto, K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 6048-6050.
3. For some representative examples, see: Kishi, Y. Pure and Appl. Chem. 1989, 61, 313-324 and references cited therein.
4. For more recent synthetic efforts on halichondrins from this laboratory, see: (a) Stamos, D. P.; Kishi, Y. Tetrahedron Lett. 1996, 37, 8643-8646; Stamos, D. P.; Taylor, A. G.; Kishi, Y. Tetrahedron Lett. 1996, 37, 8647-8650 and references cited therein, (b) Stamos, D. P., Harvard Dissertation, February, 1997.
5. For more recent synthetic efforts on halichondrins from this laboratory, see: (a) Stamos, D. P.; Kishi, Y. Tetrahedron Lett. 1996, 37, 8643-8646; Stamos, D. P.; Taylor, A. G.; Kishi, Y. Tetrahedron Lett. 1996, 37, 8647-8650 and references cited therein, (b) Stamos, D. P., Harvard Dissertation, February, 1997.
6. For more recent synthetic efforts on halichondrins from this laboratory, see: (a) Stamos, D. P.; Kishi, Y. Tetrahedron Lett. 1996, 37, 8643-8646; Stamos, D. P.; Taylor, A. G.; Kishi, Y. Tetrahedron Lett. 1996, 37, 8647-8650 and references cited therein, (b) Stamos, D. P., Harvard Dissertation, February, 1997.
7. For synthetic work from other laboratories, see: (a) Cooper, A. J.; Pan, W.; Salomon, R. G. Tetrahedron Lett. 1993, 34, 8193-8196 and references cited therein, (b) Burke, S. D.; Jung, K. W.; Phillips, J. R.; Perri, R. E. Tetrahedron Lett. 1994, 35, 703-706 and references cited therein, (c) Horita, K.; Hachiya, S.; Ogihara, K.; Yoshida, Y.; Nagasawa, M.; Yonemitsu, O. Heterocycles 1996, 42, 99-104 and references cited therein.
8. For synthetic work from other laboratories, see: (a) Cooper, A. J.; Pan, W.; Salomon, R. G. Tetrahedron Lett. 1993, 34, 8193-8196 and references cited therein, (b) Burke, S. D.; Jung, K. W.; Phillips, J. R.; Perri, R. E. Tetrahedron Lett. 1994, 35, 703-706 and references cited therein, (c) Horita, K.; Hachiya, S.; Ogihara, K.; Yoshida, Y.; Nagasawa, M.; Yonemitsu, O. Heterocycles 1996, 42, 99-104 and references cited therein.
9. For synthetic work from other laboratories, see: (a) Cooper, A. J.; Pan, W.; Salomon, R. G. Tetrahedron Lett. 1993, 34, 8193-8196 and references cited therein, (b) Burke, S. D.; Jung, K. W.; Phillips, J. R.; Perri, R. E. Tetrahedron Lett. 1994, 35, 703-706 and references cited therein, (c) Horita, K.; Hachiya, S.; Ogihara, K.; Yoshida, Y.; Nagasawa, M.; Yonemitsu, O. Heterocycles 1996, 42, 99-104 and references cited therein.
10. For a new synthetic route to the C.14-C.38 segment of halichondrin through this type of intermediates, see the reference 3b.
11. The vinyl iodide 2 was used as a 3:2 mixture of E- and Z-unsaturated esters. In the corresponding methyl ester series, both E- and Z-unsaturated esters were shown to give the same stereoselectivity in the Ni(II)/Cr(II)-mediated coupling.
12. Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem. 1995, 60, 5386-5387.
13. 1,2
14. Using 4-t-BuPy alone does not provide a homogeneous solution of CrCl2.
15. This coupling was done by dissolving 4 and 5 in THF, followed by addition of 4-t-BuPy and then a premixed mixture of NiCl2 (2%)/CrCl2 (98%) in one portion, and being stirred in the drybox at room temperature. The aldol/dehydration product i was the only detectable by-product. This by-product was formed only when chromium ion was present, implying that the Lewis acidic nature of chromium ion was necessary to promote enolization. Interestingly, formation of i was most prevalent with lower amounts of 4-t-BuPy. (figure presented)
16. For synthetic work from this laboratory, see: Kress, M. H.; Kishi, Y. Tetrahedron Lett. 1995, 36, 4583-4584 and references cited therein.
17. For completed total syntheses of taxol, see: (a) Holton, R. A.; Kim, H-B.; Somoza, C.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1599-1600 and references cited therein, (b) Nicolaou, K. C.; Ueno, H.; Liu, J-J.; Nantermet, P. G.; Yang, Z.; Renaud, J.; Paulvannan, K.; Chadha, R. J. Am. Chem. Soc. 1995, 117, 653-659 and references cited therein, (c) Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, M. J. J. Am. Chem. Soc. 1996, 118, 2843-2859 and references cited therein, (d) Wender, P. A.; Badham, N. F.; Conway, S. P.; Floreancig, P. E.; Glass, T.E.; Houze, J. B.; Krauss, N. E.; Lee, D.; Marquess, D. G.; McGrane, P. L.; Meng, W.; Natchus, M. G.; Shuker, A. J.; Sutton, J. C.; Taylor, R. E. J. Am. Chem. Soc. 1997, 119, 2757-2758 and references cited therein. For a total synthesis of (±)-taxusin, see: Hara, R.; Furukawa, T.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1996, 118, 9186-9187.
18. For completed total syntheses of taxol, see: (a) Holton, R. A.; Kim, H-B.; Somoza, C.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1599-1600 and references cited therein, (b) Nicolaou, K. C.; Ueno, H.; Liu, J-J.; Nantermet, P. G.; Yang, Z.; Renaud, J.; Paulvannan, K.; Chadha, R. J. Am. Chem. Soc. 1995, 117, 653-659 and references cited therein, (c) Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, M. J. J. Am. Chem. Soc. 1996, 118, 2843-2859 and references cited therein, (d) Wender, P. A.; Badham, N. F.; Conway, S. P.; Floreancig, P. E.; Glass, T.E.; Houze, J. B.; Krauss, N. E.; Lee, D.; Marquess, D. G.; McGrane, P. L.; Meng, W.; Natchus, M. G.; Shuker, A. J.; Sutton, J. C.; Taylor, R. E. J. Am. Chem. Soc. 1997, 119, 2757-2758 and references cited therein. For a total synthesis of (±)-taxusin, see: Hara, R.; Furukawa, T.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1996, 118, 9186-9187.
19. For completed total syntheses of taxol, see: (a) Holton, R. A.; Kim, H-B.; Somoza, C.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1599-1600 and references cited therein, (b) Nicolaou, K. C.; Ueno, H.; Liu, J-J.; Nantermet, P. G.; Yang, Z.; Renaud, J.; Paulvannan, K.; Chadha, R. J. Am. Chem. Soc. 1995, 117, 653-659 and references cited therein, (c) Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, M. J. J. Am. Chem. Soc. 1996, 118, 2843-2859 and references cited therein, (d) Wender, P. A.; Badham, N. F.; Conway, S. P.; Floreancig, P. E.; Glass, T.E.; Houze, J. B.; Krauss, N. E.; Lee, D.; Marquess, D. G.; McGrane, P. L.; Meng, W.; Natchus, M. G.; Shuker, A. J.; Sutton, J. C.; Taylor, R. E. J. Am. Chem. Soc. 1997, 119, 2757-2758 and references cited therein. For a total synthesis of (±)-taxusin, see: Hara, R.; Furukawa, T.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1996, 118, 9186-9187.
20. For completed total syntheses of taxol, see: (a) Holton, R. A.; Kim, H-B.; Somoza, C.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1599-1600 and references cited therein, (b) Nicolaou, K. C.; Ueno, H.; Liu, J-J.; Nantermet, P. G.; Yang, Z.; Renaud, J.; Paulvannan, K.; Chadha, R. J. Am. Chem. Soc. 1995, 117, 653-659 and references cited therein, (c) Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, M. J. J. Am. Chem. Soc. 1996, 118, 2843-2859 and references cited therein, (d) Wender, P. A.; Badham, N. F.; Conway, S. P.; Floreancig, P. E.; Glass, T.E.; Houze, J. B.; Krauss, N. E.; Lee, D.; Marquess, D. G.; McGrane, P. L.; Meng, W.; Natchus, M. G.; Shuker, A. J.; Sutton, J. C.; Taylor, R. E. J. Am. Chem. Soc. 1997, 119, 2757-2758 and references cited therein. For a total synthesis of (±)-taxusin, see: Hara, R.; Furukawa, T.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1996, 118, 9186-9187.
21. For completed total syntheses of taxol, see: (a) Holton, R. A.; Kim, H-B.; Somoza, C.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1599-1600 and references cited therein, (b) Nicolaou, K. C.; Ueno, H.; Liu, J-J.; Nantermet, P. G.; Yang, Z.; Renaud, J.; Paulvannan, K.; Chadha, R. J. Am. Chem. Soc. 1995, 117, 653-659 and references cited therein, (c) Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, M. J. J. Am. Chem. Soc. 1996, 118, 2843-2859 and references cited therein, (d) Wender, P. A.; Badham, N. F.; Conway, S. P.; Floreancig, P. E.; Glass, T.E.; Houze, J. B.; Krauss, N. E.; Lee, D.; Marquess, D. G.; McGrane, P. L.; Meng, W.; Natchus, M. G.; Shuker, A. J.; Sutton, J. C.; Taylor, R. E. J. Am. Chem. Soc. 1997, 119, 2757-2758 and references cited therein. For a total synthesis of (±)-taxusin, see: Hara, R.; Furukawa, T.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1996, 118, 9186-9187.
22. Kress, M. H., Harvard Dissertation, January, 1995.
23. In a typical workup, the crude reaction mixture is diluted with a 1/1 (v/v) mixture of hexanes and ethyl acetate, treated with a 1.0 M solution of sodium or potassium serinate (pH adjusted around 8 by mixing aq. sodium or potassium bicarbonate and d,l-serine), and vigorously stirred for 15∼20 minutes. Separation and washing of the aqueous phase once more with hexanes/ethyl acetate provides a clear organic phase and a deep purple aqueous phase. In the case that 4-t-BuPy is used as an additive, the combined organic phases are then washed with 3.5 M NaHSO4 (aq.) to remove 4-t-BuPy.