Synthesis of the tricarbonyl subunit (C8-C19) of rapamycin via tandem chan rearrangement-oxidation

Journal of Organic Chemistry

Volumn 61, Issue 8, 1996, Pages 2600-2601

  White, James D ^a   Jeffrey, Scott C ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

RAPAMYCIN;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029893354     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960176c     Document Type: Article

References (41)

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4. However, for a recent example, see: Holton R. A. et al. J. Am. Chem. Soc. 1994, 116, 1597.
5. Total syntheses: (a) Nicolaou, K. C.; Chakraborty, T. K.; Piscopio, A. D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc. 1993, 115, 4419. (b) Romo, D.; Meyer, S. D.; Johnson, D. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 7906. (c) Hayward, C. M.; Yohannes, D.; Danishefsky, S. J. J. Am. Chem. Soc. 1993, 115, 9345. (d) Smith, A. B., III; Condon, S. M.; McCauley, J. A ; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am Chem. Soc. 1995, 117, 5407.
6. Total syntheses: (a) Nicolaou, K. C.; Chakraborty, T. K.; Piscopio, A. D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc. 1993, 115, 4419. (b) Romo, D.; Meyer, S. D.; Johnson, D. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 7906. (c) Hayward, C. M.; Yohannes, D.; Danishefsky, S. J. J. Am. Chem. Soc. 1993, 115, 9345. (d) Smith, A. B., III; Condon, S. M.; McCauley, J. A ; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am Chem. Soc. 1995, 117, 5407.
7. Total syntheses: (a) Nicolaou, K. C.; Chakraborty, T. K.; Piscopio, A. D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc. 1993, 115, 4419. (b) Romo, D.; Meyer, S. D.; Johnson, D. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 7906. (c) Hayward, C. M.; Yohannes, D.; Danishefsky, S. J. J. Am. Chem. Soc. 1993, 115, 9345. (d) Smith, A. B., III; Condon, S. M.; McCauley, J. A ; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am Chem. Soc. 1995, 117, 5407.
8. Total syntheses: (a) Nicolaou, K. C.; Chakraborty, T. K.; Piscopio, A. D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc. 1993, 115, 4419. (b) Romo, D.; Meyer, S. D.; Johnson, D. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 7906. (c) Hayward, C. M.; Yohannes, D.; Danishefsky, S. J. J. Am. Chem. Soc. 1993, 115, 9345. (d) Smith, A. B., III; Condon, S. M.; McCauley, J. A ; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am Chem. Soc. 1995, 117, 5407.
9. Approaches to the tricarbonyl segment of rapamycin and FK-506: (a) Kocienski, P.; Stocks, M.; Donald, D.; Cooper, M.; Manners, A. Tetrahedron Lett. 1988, 29, 4481. (b) Williams, D. R.; Benbow, J. W. J. Org. Chem. 1988, 53, 4643. (c) Egbertson, M.; Danishefsky, S. J. J. Org. Chem. 1989, 54, 11. (d) Wasserman, H. H.; Rotello, V. M.; Williams, D. R.; Benbow, J. W. J. Org. Chem. 1989, 34, 2785. (e) Rama Rao, A. V.; Chakraborty, T. K.; Laxma Reddy, K Tetrahedron Lett. 1990, 31, 1439. (f) Linde, R. G., II; Jeroncic, L. O.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 2534. (g) Hoffman, R. V.; Huizenga, D. J. J. Org. Chem. 1991, 56, 6435. (h) Batchelor, M. J.; Gillespie, R. J.; Golec, J. M. C.; Hedgecock, C. J. R. Tetrahedron Lett. 1993, 34, 167. (i) Pattenden, G.; Tankard, M. Tetrahedron Lett. 1993, 34, 2677. (j) Rama Rao, A. V.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111.
10. Approaches to the tricarbonyl segment of rapamycin and FK-506: (a) Kocienski, P.; Stocks, M.; Donald, D.; Cooper, M.; Manners, A. Tetrahedron Lett. 1988, 29, 4481. (b) Williams, D. R.; Benbow, J. W. J. Org. Chem. 1988, 53, 4643. (c) Egbertson, M.; Danishefsky, S. J. J. Org. Chem. 1989, 54, 11. (d) Wasserman, H. H.; Rotello, V. M.; Williams, D. R.; Benbow, J. W. J. Org. Chem. 1989, 34, 2785. (e) Rama Rao, A. V.; Chakraborty, T. K.; Laxma Reddy, K Tetrahedron Lett. 1990, 31, 1439. (f) Linde, R. G., II; Jeroncic, L. O.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 2534. (g) Hoffman, R. V.; Huizenga, D. J. J. Org. Chem. 1991, 56, 6435. (h) Batchelor, M. J.; Gillespie, R. J.; Golec, J. M. C.; Hedgecock, C. J. R. Tetrahedron Lett. 1993, 34, 167. (i) Pattenden, G.; Tankard, M. Tetrahedron Lett. 1993, 34, 2677. (j) Rama Rao, A. V.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111.
11. Approaches to the tricarbonyl segment of rapamycin and FK-506: (a) Kocienski, P.; Stocks, M.; Donald, D.; Cooper, M.; Manners, A. Tetrahedron Lett. 1988, 29, 4481. (b) Williams, D. R.; Benbow, J. W. J. Org. Chem. 1988, 53, 4643. (c) Egbertson, M.; Danishefsky, S. J. J. Org. Chem. 1989, 54, 11. (d) Wasserman, H. H.; Rotello, V. M.; Williams, D. R.; Benbow, J. W. J. Org. Chem. 1989, 34, 2785. (e) Rama Rao, A. V.; Chakraborty, T. K.; Laxma Reddy, K Tetrahedron Lett. 1990, 31, 1439. (f) Linde, R. G., II; Jeroncic, L. O.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 2534. (g) Hoffman, R. V.; Huizenga, D. J. J. Org. Chem. 1991, 56, 6435. (h) Batchelor, M. J.; Gillespie, R. J.; Golec, J. M. C.; Hedgecock, C. J. R. Tetrahedron Lett. 1993, 34, 167. (i) Pattenden, G.; Tankard, M. Tetrahedron Lett. 1993, 34, 2677. (j) Rama Rao, A. V.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111.
12. Approaches to the tricarbonyl segment of rapamycin and FK-506: (a) Kocienski, P.; Stocks, M.; Donald, D.; Cooper, M.; Manners, A. Tetrahedron Lett. 1988, 29, 4481. (b) Williams, D. R.; Benbow, J. W. J. Org. Chem. 1988, 53, 4643. (c) Egbertson, M.; Danishefsky, S. J. J. Org. Chem. 1989, 54, 11. (d) Wasserman, H. H.; Rotello, V. M.; Williams, D. R.; Benbow, J. W. J. Org. Chem. 1989, 34, 2785. (e) Rama Rao, A. V.; Chakraborty, T. K.; Laxma Reddy, K Tetrahedron Lett. 1990, 31, 1439. (f) Linde, R. G., II; Jeroncic, L. O.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 2534. (g) Hoffman, R. V.; Huizenga, D. J. J. Org. Chem. 1991, 56, 6435. (h) Batchelor, M. J.; Gillespie, R. J.; Golec, J. M. C.; Hedgecock, C. J. R. Tetrahedron Lett. 1993, 34, 167. (i) Pattenden, G.; Tankard, M. Tetrahedron Lett. 1993, 34, 2677. (j) Rama Rao, A. V.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111.
13. Approaches to the tricarbonyl segment of rapamycin and FK-506: (a) Kocienski, P.; Stocks, M.; Donald, D.; Cooper, M.; Manners, A. Tetrahedron Lett. 1988, 29, 4481. (b) Williams, D. R.; Benbow, J. W. J. Org. Chem. 1988, 53, 4643. (c) Egbertson, M.; Danishefsky, S. J. J. Org. Chem. 1989, 54, 11. (d) Wasserman, H. H.; Rotello, V. M.; Williams, D. R.; Benbow, J. W. J. Org. Chem. 1989, 34, 2785. (e) Rama Rao, A. V.; Chakraborty, T. K.; Laxma Reddy, K Tetrahedron Lett. 1990, 31, 1439. (f) Linde, R. G., II; Jeroncic, L. O.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 2534. (g) Hoffman, R. V.; Huizenga, D. J. J. Org. Chem. 1991, 56, 6435. (h) Batchelor, M. J.; Gillespie, R. J.; Golec, J. M. C.; Hedgecock, C. J. R. Tetrahedron Lett. 1993, 34, 167. (i) Pattenden, G.; Tankard, M. Tetrahedron Lett. 1993, 34, 2677. (j) Rama Rao, A. V.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111.
14. Approaches to the tricarbonyl segment of rapamycin and FK-506: (a) Kocienski, P.; Stocks, M.; Donald, D.; Cooper, M.; Manners, A. Tetrahedron Lett. 1988, 29, 4481. (b) Williams, D. R.; Benbow, J. W. J. Org. Chem. 1988, 53, 4643. (c) Egbertson, M.; Danishefsky, S. J. J. Org. Chem. 1989, 54, 11. (d) Wasserman, H. H.; Rotello, V. M.; Williams, D. R.; Benbow, J. W. J. Org. Chem. 1989, 34, 2785. (e) Rama Rao, A. V.; Chakraborty, T. K.; Laxma Reddy, K Tetrahedron Lett. 1990, 31, 1439. (f) Linde, R. G., II; Jeroncic, L. O.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 2534. (g) Hoffman, R. V.; Huizenga, D. J. J. Org. Chem. 1991, 56, 6435. (h) Batchelor, M. J.; Gillespie, R. J.; Golec, J. M. C.; Hedgecock, C. J. R. Tetrahedron Lett. 1993, 34, 167. (i) Pattenden, G.; Tankard, M. Tetrahedron Lett. 1993, 34, 2677. (j) Rama Rao, A. V.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111.
15. Approaches to the tricarbonyl segment of rapamycin and FK-506: (a) Kocienski, P.; Stocks, M.; Donald, D.; Cooper, M.; Manners, A. Tetrahedron Lett. 1988, 29, 4481. (b) Williams, D. R.; Benbow, J. W. J. Org. Chem. 1988, 53, 4643. (c) Egbertson, M.; Danishefsky, S. J. J. Org. Chem. 1989, 54, 11. (d) Wasserman, H. H.; Rotello, V. M.; Williams, D. R.; Benbow, J. W. J. Org. Chem. 1989, 34, 2785. (e) Rama Rao, A. V.; Chakraborty, T. K.; Laxma Reddy, K Tetrahedron Lett. 1990, 31, 1439. (f) Linde, R. G., II; Jeroncic, L. O.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 2534. (g) Hoffman, R. V.; Huizenga, D. J. J. Org. Chem. 1991, 56, 6435. (h) Batchelor, M. J.; Gillespie, R. J.; Golec, J. M. C.; Hedgecock, C. J. R. Tetrahedron Lett. 1993, 34, 167. (i) Pattenden, G.; Tankard, M. Tetrahedron Lett. 1993, 34, 2677. (j) Rama Rao, A. V.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111.
16. Approaches to the tricarbonyl segment of rapamycin and FK-506: (a) Kocienski, P.; Stocks, M.; Donald, D.; Cooper, M.; Manners, A. Tetrahedron Lett. 1988, 29, 4481. (b) Williams, D. R.; Benbow, J. W. J. Org. Chem. 1988, 53, 4643. (c) Egbertson, M.; Danishefsky, S. J. J. Org. Chem. 1989, 54, 11. (d) Wasserman, H. H.; Rotello, V. M.; Williams, D. R.; Benbow, J. W. J. Org. Chem. 1989, 34, 2785. (e) Rama Rao, A. V.; Chakraborty, T. K.; Laxma Reddy, K Tetrahedron Lett. 1990, 31, 1439. (f) Linde, R. G., II; Jeroncic, L. O.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 2534. (g) Hoffman, R. V.; Huizenga, D. J. J. Org. Chem. 1991, 56, 6435. (h) Batchelor, M. J.; Gillespie, R. J.; Golec, J. M. C.; Hedgecock, C. J. R. Tetrahedron Lett. 1993, 34, 167. (i) Pattenden, G.; Tankard, M. Tetrahedron Lett. 1993, 34, 2677. (j) Rama Rao, A. V.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111.
17. Approaches to the tricarbonyl segment of rapamycin and FK-506: (a) Kocienski, P.; Stocks, M.; Donald, D.; Cooper, M.; Manners, A. Tetrahedron Lett. 1988, 29, 4481. (b) Williams, D. R.; Benbow, J. W. J. Org. Chem. 1988, 53, 4643. (c) Egbertson, M.; Danishefsky, S. J. J. Org. Chem. 1989, 54, 11. (d) Wasserman, H. H.; Rotello, V. M.; Williams, D. R.; Benbow, J. W. J. Org. Chem. 1989, 34, 2785. (e) Rama Rao, A. V.; Chakraborty, T. K.; Laxma Reddy, K Tetrahedron Lett. 1990, 31, 1439. (f) Linde, R. G., II; Jeroncic, L. O.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 2534. (g) Hoffman, R. V.; Huizenga, D. J. J. Org. Chem. 1991, 56, 6435. (h) Batchelor, M. J.; Gillespie, R. J.; Golec, J. M. C.; Hedgecock, C. J. R. Tetrahedron Lett. 1993, 34, 167. (i) Pattenden, G.; Tankard, M. Tetrahedron Lett. 1993, 34, 2677. (j) Rama Rao, A. V.; Desibhatla, V. Tetrahedron Lett. 1993, 34, 7111.
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