Stereoselective synthesis of an A-seco-taxoid subunit using the aldol- annelation-fragmentation strategy

Tetrahedron Letters

Volumn 39, Issue 40, 1998, Pages 7291-7294

  Arseniyadis, Siméon ^a   Rico Ferreira, María Del Rosario ^a   Quílez Del Moral, José ^a   Hernando, José Ignacio Martín ^a   Potier, Pierre ^a   Toupet, Loïc ^b  

^a CNRS   (France)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

TAXOID;

ARTICLE; DERIVATIZATION; DRUG SYNTHESIS; ENANTIOMER; ENZYME SUBUNIT; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0032192213     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01560-3     Document Type: Article

References (14)

1. 1. Review articles: Nicolaou, K. C.; Dai, W. M.; Guy, R. K. Angew. Chem. Int. Ed. Engl. 1994, 33, 15-44; Boa, A. N.; Jenkins, P. R. and Lawrence, N. J. Contemporary Organic Synthesis 1994, 1, 47-75.
2. 1. Review articles: Nicolaou, K. C.; Dai, W. M.; Guy, R. K. Angew. Chem. Int. Ed. Engl. 1994, 33, 15-44; Boa, A. N.; Jenkins, P. R. and Lawrence, N. J. Contemporary Organic Synthesis 1994, 1, 47-75.
3. 2. Arseniyadis, S.; Rico Ferreira, M.; Quilez del Moral, J.; Yashunsky, D.V.; Potier, P. Tetrahedron Lett. 1998, 39, 571-574 and references cited therein.
4. 3. This retrosynthesis did not account for the stereogenic center at C-3; however, we anticipated that this center could be controlled by equilibration after closure to the taxoid ABC system.
5. 4 Arseniyadis, S.; Rodriguez, R.; Muñoz Dorado, M.; Brondi Alves, R.; Ouazzani, J.; Ourisson, G. Tetrahedron 1994, 50, 8399-8426.
6. 5. Grob, C. A.; Baumann, W. Helv. Chim. Acta 1955, 38, 594; Clayton, R. B.; Henbest, H. B.; Smith, M. J. Chem. Soc. 1957, 1983-1993; Wharton, P. S. J. Org. Chem. 1961, 26, 4781-4782.
7. 5. Grob, C. A.; Baumann, W. Helv. Chim. Acta 1955, 38, 594; Clayton, R. B.; Henbest, H. B.; Smith, M. J. Chem. Soc. 1957, 1983-1993; Wharton, P. S. J. Org. Chem. 1961, 26, 4781-4782.
8. 5. Grob, C. A.; Baumann, W. Helv. Chim. Acta 1955, 38, 594; Clayton, R. B.; Henbest, H. B.; Smith, M. J. Chem. Soc. 1957, 1983-1993; Wharton, P. S. J. Org. Chem. 1961, 26, 4781-4782.
9. 10 m/z 600.2935 found: 600.2938.
10. 7. Herrmann, W. A.; Fischer, R. W.; Marz, D. W. Angew. Chem. Int. Ed. Engl. 1991, 30, 1638-1641; Herrmann, W. A. J. Organomet. Chem. 1995, 500, 149; Herrmann, W. A.; Fischer, R. W.; Rauch, M. U.; Scherer, W. J. Mol. Catal. 1994, 86, 243; Herrmann, W. A.; Kuhn, F. E. Acc. Chem. Res. 1997, 30, 169-180; Rudolph, J.; Reddy, K. L.; Chiang, J. P.; Sharpless, B. J. Am. Chem. Soc. 1997, 119, 6189-6190.
11. 7. Herrmann, W. A.; Fischer, R. W.; Marz, D. W. Angew. Chem. Int. Ed. Engl. 1991, 30, 1638-1641; Herrmann, W. A. J. Organomet. Chem. 1995, 500, 149; Herrmann, W. A.; Fischer, R. W.; Rauch, M. U.; Scherer, W. J. Mol. Catal. 1994, 86, 243; Herrmann, W. A.; Kuhn, F. E. Acc. Chem. Res. 1997, 30, 169-180; Rudolph, J.; Reddy, K. L.; Chiang, J. P.; Sharpless, B. J. Am. Chem. Soc. 1997, 119, 6189-6190.
12. 7. Herrmann, W. A.; Fischer, R. W.; Marz, D. W. Angew. Chem. Int. Ed. Engl. 1991, 30, 1638-1641; Herrmann, W. A. J. Organomet. Chem. 1995, 500, 149; Herrmann, W. A.; Fischer, R. W.; Rauch, M. U.; Scherer, W. J. Mol. Catal. 1994, 86, 243; Herrmann, W. A.; Kuhn, F. E. Acc. Chem. Res. 1997, 30, 169-180; Rudolph, J.; Reddy, K. L.; Chiang, J. P.; Sharpless, B. J. Am. Chem. Soc. 1997, 119, 6189-6190.
13. 7. Herrmann, W. A.; Fischer, R. W.; Marz, D. W. Angew. Chem. Int. Ed. Engl. 1991, 30, 1638-1641; Herrmann, W. A. J. Organomet. Chem. 1995, 500, 149; Herrmann, W. A.; Fischer, R. W.; Rauch, M. U.; Scherer, W. J. Mol. Catal. 1994, 86, 243; Herrmann, W. A.; Kuhn, F. E. Acc. Chem. Res. 1997, 30, 169-180; Rudolph, J.; Reddy, K. L.; Chiang, J. P.; Sharpless, B. J. Am. Chem. Soc. 1997, 119, 6189-6190.
14. 7. Herrmann, W. A.; Fischer, R. W.; Marz, D. W. Angew. Chem. Int. Ed. Engl. 1991, 30, 1638-1641; Herrmann, W. A. J. Organomet. Chem. 1995, 500, 149; Herrmann, W. A.; Fischer, R. W.; Rauch, M. U.; Scherer, W. J. Mol. Catal. 1994, 86, 243; Herrmann, W. A.; Kuhn, F. E. Acc. Chem. Res. 1997, 30, 169-180; Rudolph, J.; Reddy, K. L.; Chiang, J. P.; Sharpless, B. J. Am. Chem. Soc. 1997, 119, 6189-6190.