An expedient access to highly functionalized B-seco taxoid frameworks

Tetrahedron Letters

Volumn 39, Issue 21, 1998, Pages 3489-3492

  Arseniyadis, S ^a   Martin Hernando, J I ^a   Quilez Del Moral, J ^a   Yashunsky, D V ^a   Potier, P ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; TAXOID;

ARTICLE; CHEMICAL ANALYSIS; HYPOTHESIS; METHODOLOGY; OXIDATION; SYNTHESIS;

EID: 0032554986     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00600-5     Document Type: Article

References (14)

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2. Arseniyadis, S.; Brondi Alves R.; Pereira de Freitas, R.; Muñoz-Dorado M.; Yashunsky, D. V.; Potier, P.; Toupet, L. Heterocycles 1997, 46, 727-764.
3. Review articles: Boa, A. N.; Jenkins, P. R. and Lawrence, N. J. Contemporary Organic Synthesis 1994, 1, 47-75;
4. Nicolaou, K. C.; Dai, W. M.; Guy, R. K. Angew. Chem. Int. Ed. Engl. 1994, 33, 15-44.
5. Still, W. C. J. Am. Chem. Soc., 1978, 100, 1481-1486.
6. Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651-1660.
7. 3CN, also afforded the desired aldehyde 10, but we could not avoid partial further oxidation to the corresponding carboxylic acid during purification: Ley, S. V.; Norman, J. ; Griffith, W. P.; Marsden, S. P. Synthesis, 1994, 639;
8. Griffith, W. P.; Ley, S. V. Aldrichimica Acta 1990, 23, 13.
9. Tanaka, A.; Yamamoto, H.; Oritani, T. Tetrahedron : Asymmetry, 1995, 6, 1273-1278.
10. Organometallic carbon nucleophiles generally react with carbon electrophiles with retention of configuration: Still, W. C.; Sreekumar, C. J. Am. Chem. Soc., 1980, 102, 1201-1202;
11. Sawyer, J. S.; Macdonald, T. L.; McGarvey, G. J. J. Am. Chem. Soc. 1984, 106, 3376-3377.
12. 2O, 100). The C-10 configuration remains unknown for all the compounds investigated.
13. Transformation of the model allylic tertiary alcohol 12 to the transposed α, β-unsaturated ketone 13 was carried out according to: Dauben, W. G.; Michno, D. M. J. Org. Chem. 1977, 42, 682-685. (Chemical Equation Presented)
14. 3.