Synthesis of a diterpene taxoid skeleton, bicyclo[9.3.1]pentadecatriene

Tetrahedron

Volumn 54, Issue 24, 1998, Pages 6677-6698

  Shibuya, Satoshi ^a   Isobe, Minoru ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENOID; TAXOID;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CYCLIZATION; DRUG ACTIVITY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; MEDICINAL PLANT; METHODOLOGY; PRIORITY JOURNAL;

EID: 0032507904     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00334-2     Document Type: Article

References (37)

1. 1. Fang, W.-S.; Fang, Q.-C.; Liang, X.-T.; Lu, Y.; Zheng, Q.-T. Tetrahedron 1995, 51, 8483-8490.
2. 2. Fang, W.-S.; Fang, Q.-C.; Liang, X.-T. Planta Med. 1996, 62, 567-569.
3. 3. Zamir, L. O.; Zhou, Z. H.; Caron, G.; Nedea, M. E.; Sauriol, F.; Mamer, O. J. Chem. Soc., Chem. Commun. 1995, 529-530.
4. 4. Boulanger, Y.; Khiat, A.; Zhou, Z.-H.; Caron, G.; Zamir, L. O. Tetrahedron 1996, 52, 8957-8968.
5. 5. Rohr, J. Angew. Chem. Int. Ed. Engl. 1997, 36, 2190-2195, and those references cited therein.
6. 6. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325-2327.
7. 7. Holten, R. A.; Somoza, C.; Kim, H. -B.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 776, 1597-1598.
8. 8. Holton, R. A.; Kim, H.-B.; Sozoma, C.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1599-1600.
9. 9. Nicolaou, K. C.; Yang, Z.; Liu, J. J.; Ueno, H.; Nantermet, P. G.; Guy, R. K.; Claiborne, C. F.; Renaud, J.; Couladouros, E. A.; Paulvannan, K.; Sorensen, E. J. Nature 1994, 367, 630-634.
10. 10. Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem. Int. Ed. Engl. 1995, 34, 1723-1726.
11. 11. Wender, P. A.; Badham, N. F.; Conway, S. P.; Floreancig, P. E.; Glass, T. E.; Gränicher, C.; Houze, J. B.; Jänichen, J.; Lee, D.; Marquess, D. G.; McGrane, P. L.; Meng, W.; Mucciaro, T. P.; Mühlebach, M.; Natchus, M. G.; Paulsen, H.; Rawlins, D. B.; Satkofsky, J.; Shuker, A. J.; Sutton, J. C.; Taylor, R. E.; Tomooka, K. J. Am. Chem. Soc. 1997, 119, 2755-2756.
12. 12. 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.
13. 13. Mukaiyama, T.; Shiina, I.; Iwadare, H.; Sakoh, H.; Tani, Y.; Hasegawa, M.; Saitoh, K. Proc. Japan Acad. 1997, 73, Ser. B, 95-100.
14. 14. Holton, R. A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668.
15. 15. Ojima, I.; Habus, I.; Zhao, M. J. Org. Chem. 1991, 56, 1681-1683.
16. 16. Shibuya, S.; Isobe, M. Synlett 1998, in press.
17. 17. Connor, R. E.; Nicholas, K. M. J. Organomet. Chem. 1977, 125, C45-C48.
18. 18. Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207-214, and references cited therein.
19. 19. Di Grandi, M. J.; Jung, D. K.; Krol, W. J.; Danishefsky, S. J. J. Org Chem. 1993, 58, 989-4992.
20. 20. Barton, D. H. R.; Bashiardes, G.; Fourrey, J.-L., Tetrahedron, 1988, 44, 147-162.
21. 21. Cymerman, J.; Heilbron, I. M.; Jones, E. R. H. J. Chem. Soc. 1945, 90-94.
22. 22. Smith, J. G.; Drozda, S. E.; Petraglia, S. P.; Quinn, N. R.; Rice, E. M.; Taylor, B. S.; Viswanathan, M. J. Org. Chem. 1984, 49, 4112-4120.
23. 23. Still, W. C. J. Org. Chem. 1976, 41, 3063-3064. Smith, J. G.; Drozda, S. E.; Petraglia, S. P.; Quinn, N. R.; Rice, E. M.; Taylor, B. S.; Viswanathan, M. J. Org. Chem. 1984, 49, 4112-4120.
24. 23. Still, W. C. J. Org. Chem. 1976, 41, 3063-3064. Smith, J. G.; Drozda, S. E.; Petraglia, S. P.; Quinn, N. R.; Rice, E. M.; Taylor, B. S.; Viswanathan, M. J. Org. Chem. 1984, 49, 4112-4120.
25. 24. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470.
26. 25. Our laboratory reported the synthesis of 10 using different pathway. Bamba, M.; Nishikawa, T.; Isobe, M. Tetrahedron Lett. 1996, 37, 8199-8202.
27. 26. Padmanabhan, S.; Nicholas, K. M. Tetrahedron Lett. 1982, 23, 2555-2558.
28. 8. The acetylene also resisted hydrogenation in the presence of Lindler catalyst, hydrosilation and hydrostannylation.
29. 2/THF-TMEDA) with side-product that was difficult to separate from 28. After the mixture reacted with fragment 9, the coupling product 29 was able to be purified.
30. 29. Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128-3130.
31. 30. Nakamura, T.; Matsui, T.; Tanino, K.; Kuwajima, I. J. Org. Chem. 1997, 62, 3032-3033.
32. 31. Bisacetylene 36 was treated with 1 equivalent of dicobalt octacarbonyl to give three products; both acetylenes of 36 were produced cobalt complex, one of two acetylenes of 36 was produced cobalt complex, respectively. The ratio of three compounds was almost 1:1:1.
33. 32. These improvements are not only because of the leaving groups. The stability of the precursor itself also is important. Compounds 41 and 42 are more stable than 38.
34. 33. Hosokawa, S.; Isobe, M. Synlett 1996, 351-352.
35. 34. Isobe, M.; Hosokawa, S.; Kira, K. Chem. Lett. 1996, 473-474.
36. 35. Hosokawa, S.; Isobe, M. Tetrahedron Lett. 1998, in press.
37. 36. exo-Cyclic acetylene cobalt complex was treated with excess NBS in ether solution to give the corresponding original acetylenic compound.