An approach to the synthesis of CP-263,114: A remarkably facile silyloxy-Cope rearrangement [18]

Journal of the American Chemical Society

Volumn 121, Issue 4, 1999, Pages 890-891

  Bio, Matthew M ^a   Leighton, James L ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NATURAL PRODUCT; PHOMOIDRIDE A; PHOMOIDRIDE B; PROTEIN FARNESYLTRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

CHEMICAL REACTION KINETICS; DRUG ISOLATION; DRUG SYNTHESIS; ENZYME INHIBITION; LETTER; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0033518569     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983609x     Document Type: Letter

References (29)

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5. Other approaches to the synthesis of CP-263,114 and CP-225,917: (a) Davies, H. M. L.; Calvo, R.; Ahmed, G. Tetrahedron Lett. 1997, 38, 1737-1740. (b) Nicolaou, K. C.; Härter, M. W.; Boulton, L.; Jandeleit, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1194-1196. (c) Nicolaou, K. C.; Postema, M. H. D.; Miller, N. D.; Yang, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2821-2823. (d) Sgarbi, P. W. M.; Clive, D. L. J. Chem. Commun. 1997, 2157-2158. (e) Armstrong, A.; Critchley, T. J.; Mortlook, A. A. Synlett 1998, 552-553. (f) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1877-1880. (g) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1880-1882. (h) Waizumi, N.; Itoh, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 6015-6018. (i) Chen, C.; Layton, M. E.; Shair, M. D. J. Am. Chem. Soc. 1998, 120, 10784-10785.
6. Other approaches to the synthesis of CP-263,114 and CP-225,917: (a) Davies, H. M. L.; Calvo, R.; Ahmed, G. Tetrahedron Lett. 1997, 38, 1737-1740. (b) Nicolaou, K. C.; Härter, M. W.; Boulton, L.; Jandeleit, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1194-1196. (c) Nicolaou, K. C.; Postema, M. H. D.; Miller, N. D.; Yang, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2821-2823. (d) Sgarbi, P. W. M.; Clive, D. L. J. Chem. Commun. 1997, 2157-2158. (e) Armstrong, A.; Critchley, T. J.; Mortlook, A. A. Synlett 1998, 552-553. (f) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1877-1880. (g) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1880-1882. (h) Waizumi, N.; Itoh, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 6015-6018. (i) Chen, C.; Layton, M. E.; Shair, M. D. J. Am. Chem. Soc. 1998, 120, 10784-10785.
7. Other approaches to the synthesis of CP-263,114 and CP-225,917: (a) Davies, H. M. L.; Calvo, R.; Ahmed, G. Tetrahedron Lett. 1997, 38, 1737-1740. (b) Nicolaou, K. C.; Härter, M. W.; Boulton, L.; Jandeleit, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1194-1196. (c) Nicolaou, K. C.; Postema, M. H. D.; Miller, N. D.; Yang, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2821-2823. (d) Sgarbi, P. W. M.; Clive, D. L. J. Chem. Commun. 1997, 2157-2158. (e) Armstrong, A.; Critchley, T. J.; Mortlook, A. A. Synlett 1998, 552-553. (f) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1877-1880. (g) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1880-1882. (h) Waizumi, N.; Itoh, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 6015-6018. (i) Chen, C.; Layton, M. E.; Shair, M. D. J. Am. Chem. Soc. 1998, 120, 10784-10785.
8. Other approaches to the synthesis of CP-263,114 and CP-225,917: (a) Davies, H. M. L.; Calvo, R.; Ahmed, G. Tetrahedron Lett. 1997, 38, 1737-1740. (b) Nicolaou, K. C.; Härter, M. W.; Boulton, L.; Jandeleit, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1194-1196. (c) Nicolaou, K. C.; Postema, M. H. D.; Miller, N. D.; Yang, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2821-2823. (d) Sgarbi, P. W. M.; Clive, D. L. J. Chem. Commun. 1997, 2157-2158. (e) Armstrong, A.; Critchley, T. J.; Mortlook, A. A. Synlett 1998, 552-553. (f) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1877-1880. (g) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1880-1882. (h) Waizumi, N.; Itoh, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 6015-6018. (i) Chen, C.; Layton, M. E.; Shair, M. D. J. Am. Chem. Soc. 1998, 120, 10784-10785.
9. Other approaches to the synthesis of CP-263,114 and CP-225,917: (a) Davies, H. M. L.; Calvo, R.; Ahmed, G. Tetrahedron Lett. 1997, 38, 1737-1740. (b) Nicolaou, K. C.; Härter, M. W.; Boulton, L.; Jandeleit, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1194-1196. (c) Nicolaou, K. C.; Postema, M. H. D.; Miller, N. D.; Yang, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2821-2823. (d) Sgarbi, P. W. M.; Clive, D. L. J. Chem. Commun. 1997, 2157-2158. (e) Armstrong, A.; Critchley, T. J.; Mortlook, A. A. Synlett 1998, 552-553. (f) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1877-1880. (g) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1880-1882. (h) Waizumi, N.; Itoh, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 6015-6018. (i) Chen, C.; Layton, M. E.; Shair, M. D. J. Am. Chem. Soc. 1998, 120, 10784-10785.
10. Other approaches to the synthesis of CP-263,114 and CP-225,917: (a) Davies, H. M. L.; Calvo, R.; Ahmed, G. Tetrahedron Lett. 1997, 38, 1737-1740. (b) Nicolaou, K. C.; Härter, M. W.; Boulton, L.; Jandeleit, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1194-1196. (c) Nicolaou, K. C.; Postema, M. H. D.; Miller, N. D.; Yang, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2821-2823. (d) Sgarbi, P. W. M.; Clive, D. L. J. Chem. Commun. 1997, 2157-2158. (e) Armstrong, A.; Critchley, T. J.; Mortlook, A. A. Synlett 1998, 552-553. (f) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1877-1880. (g) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1880-1882. (h) Waizumi, N.; Itoh, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 6015-6018. (i) Chen, C.; Layton, M. E.; Shair, M. D. J. Am. Chem. Soc. 1998, 120, 10784-10785.
11. Other approaches to the synthesis of CP-263,114 and CP-225,917: (a) Davies, H. M. L.; Calvo, R.; Ahmed, G. Tetrahedron Lett. 1997, 38, 1737-1740. (b) Nicolaou, K. C.; Härter, M. W.; Boulton, L.; Jandeleit, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1194-1196. (c) Nicolaou, K. C.; Postema, M. H. D.; Miller, N. D.; Yang, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2821-2823. (d) Sgarbi, P. W. M.; Clive, D. L. J. Chem. Commun. 1997, 2157-2158. (e) Armstrong, A.; Critchley, T. J.; Mortlook, A. A. Synlett 1998, 552-553. (f) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1877-1880. (g) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1880-1882. (h) Waizumi, N.; Itoh, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 6015-6018. (i) Chen, C.; Layton, M. E.; Shair, M. D. J. Am. Chem. Soc. 1998, 120, 10784-10785.
12. Other approaches to the synthesis of CP-263,114 and CP-225,917: (a) Davies, H. M. L.; Calvo, R.; Ahmed, G. Tetrahedron Lett. 1997, 38, 1737-1740. (b) Nicolaou, K. C.; Härter, M. W.; Boulton, L.; Jandeleit, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1194-1196. (c) Nicolaou, K. C.; Postema, M. H. D.; Miller, N. D.; Yang, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2821-2823. (d) Sgarbi, P. W. M.; Clive, D. L. J. Chem. Commun. 1997, 2157-2158. (e) Armstrong, A.; Critchley, T. J.; Mortlook, A. A. Synlett 1998, 552-553. (f) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1877-1880. (g) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1880-1882. (h) Waizumi, N.; Itoh, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 6015-6018. (i) Chen, C.; Layton, M. E.; Shair, M. D. J. Am. Chem. Soc. 1998, 120, 10784-10785.
13. Other approaches to the synthesis of CP-263,114 and CP-225,917: (a) Davies, H. M. L.; Calvo, R.; Ahmed, G. Tetrahedron Lett. 1997, 38, 1737-1740. (b) Nicolaou, K. C.; Härter, M. W.; Boulton, L.; Jandeleit, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1194-1196. (c) Nicolaou, K. C.; Postema, M. H. D.; Miller, N. D.; Yang, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2821-2823. (d) Sgarbi, P. W. M.; Clive, D. L. J. Chem. Commun. 1997, 2157-2158. (e) Armstrong, A.; Critchley, T. J.; Mortlook, A. A. Synlett 1998, 552-553. (f) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1877-1880. (g) Kwon, O.; Su, D.-S.; Meng, D.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1880-1882. (h) Waizumi, N.; Itoh, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 6015-6018. (i) Chen, C.; Layton, M. E.; Shair, M. D. J. Am. Chem. Soc. 1998, 120, 10784-10785.
14. Evans, D. A.; Golob, A. M. J. Am. Chem. Soc. 1975, 97, 4765-4766.
15. For reviews on the Cope rearrangement, see: (a) Hill, R. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 785-826. (b) Paquette, L. A. Tetrahedron 1997, 53, 13971-14020
16. For reviews on the Cope rearrangement, see: (a) Hill, R. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 785-826. (b) Paquette, L. A. Tetrahedron 1997, 53, 13971-14020
17. A related anionic oxy-Cope rearrangement has been employed in an approach to the taxane bridgehead double bond: Martin, S. F.; White, J. B.; Wagner, R. J. Org. Chem. 1982, 47, 3190-3192.
18. Ketoacid 5 was obtained from an endo-selective Diels-Alder reaction of methyl crotonate and 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene, followed by saponification of the ester, dissolving metal reduction to remove the chlorines, and ketal hydrolysis in 81% overall yield. See the Supporting Information for details. See also: Thompson, H. W.; Wong, J. K.; Lalancette, R. A.; Boyko, J. A.; Robertiello, A. M. J. Org. Chem. 1985, 50, 2115-2121 and references therein.
19. All new compounds were characterized spectroscopically. Full details are provided in the Supporting Information.
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28. The structure of silyl enol ether 17 was determined spectroscopically including COSY and nOe experiments. All data are in full accord with the assigned structure. See the Supporting Information for details.
29. For a recent review on bridgehead or "anti-Bredt" double bonds, see: Warner, P. M. Chem. Rev. 1989, 89, 1067-1093.