A concise preparation of an appropriately functionalized B-seco taxane derivative

Synlett

Volumn , Issue 9, 1998, Pages 1010-1012

  Arseniyadis, Siméon ^a   Hernando, José Ignacio Martín ^a   Del Moral, José Quílez ^a   Yashunsky, Dmitry V ^a   Potier, Pierre ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002850493     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1833     Document Type: Article

References (17)

1. Review articles see: Boa, A. N.; Jenkins, P. R. and Lawrence, N. J. Contemporary Organic Synthesis 1994, 1, 47-75;
2. Nicolaou, K.C.; Dai, W.M.; Guy, R.K. Angew. Chem. Int. Ed. Engl. 1994, 33, 15-44;
3. Total syntheses: 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;
4. Holton, 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.; Tang, S.; Zhang, P.; Murthi, K.K.; Gentile, L.N. and Liu, J.H. J. Am. Chem. Soc. 1994, 116, 1597-1600;
5. Masters, J.J.; Link, J.T.; Snyder, L.B.; Young, W.B.; Danishefsky, S.J. Angew. Chem. Int. Ed. Engl. 1995, 34, 1723-1726;
6. Wender, P.A.; Badham, N.F.; Conway, S.P.; Floreansic, P.E.; Glass, T.E.; Houze, J.B.; Krauss, N.B.; Lee, D.; Marquess, D.J.; 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;
7. Mukaiyama, T.; Shiina, I; Iwadare, H.; Sakoh, H.; Tani, Y.; Hasegawa, M.; Saitoh, K. Proc. Japan Acad., Ser. B 1997, 73, 95-100.
8. Arseniyadis, S.; Brondi Alves R.; Pereira de Freitas, R.; Muñoz-Dorado M.; Yashunsky, D.V.; Potier, P.; Toupet, L. Heterocycles 1997, 46, 727-764.
9. Arseniyadis, S.; Yashunsky, D.V.; Pereira de Freitas, R.; Muñoz-Dorado M.; Potier, P.; Toupet, L. Tetrahedron 1996, 52, 12443-12458.
10. Optical purity was secured via our lipase-catalyzed hydrolysis rather than using the proline catalyzed asymmetric Robinson annelation: Arseniyadis, S.; Rodriguez, R.; Muñoz Dorado, M.; Brondi Alves, R.; Ouazzani, J.; Ourisson, G. Tetrahedron 1994, 50, 8399-8426.
11. Ley, S.V.; Norman, J. ; Griffith, W.P.; Marsden, S.P. Synthesis 1994, 639-666;
12. Griffith, W.P.; Ley, S.V. Aldrichimica Acta 1990, 23, 13.
13. Still, W.C. J. Am. Chem. Soc. 1978, 100, 1481-1486.
14. Tanaka, A.; Yamamoto, H.; Oritani, T. Tetrahedron: Asymmetry 1995, 6, 1273-1278.
15. Still, W.C.; Sreekumar, C. J. Am. Chem. Soc. 1980, 102, 1201-1202.
16. Organometallic carbon nucleophiles generally react with carbon electrophiles with retention of configuration: Sawyer, J. S.; Macdonald, T.L.; McGarvey, G.J. J. Am. Chem. Soc. 1984, 106, 3376-3377.
17. No efforts have been devoted to determine the absolute configuration at C-10 position of organostannanes 12a and 12b as this, and the C-11, C-14 centers on the A-C linked intermediates 14, 15 and 16 are programmed to be destroyed in later steps.