Lithiated (E)-5-tosyl-4-pentenoic acid: A new δ-acyldienyl anion equivalent

Tetrahedron Letters

Volumn 40, Issue 32, 1999, Pages 5957-5960

  Caturla, Francisco ^a   Nájera, Carmen ^a   Varea, Montserrat ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

Dienoates; Lactones; Lithiation; Sulfones

Indexed keywords

4 PENTENOIC ACID; 5 TOSYL 4 PENTENOIC ACID; CARBONYL DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DIASTEREOISOMER; ESTERIFICATION; IODINATION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033529777     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01183-1     Document Type: Article

References (26)

1. For recent reviews about polyene macrolide antibiotics see: (a) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021-2040.
2. (b) Norcross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041-2114.
3. For a recent review about natural products with polyene amide structures see: Nájera, C.; Yus, M. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science, Vol. 21 in the press.
4. Babudri, F.; Fiandanese, V.; Naso, F.; Punzi, A. Tetrahedron Lett. 1994, 35, 2067-2070.
5. Bernabeu, M. C.; Chinchilla, R.; Nájera, C. Tetrahedron Lett. 1995, 36, 3901-3904.
6. Huang, Y. Z.; Mo, X. S. Synlett 1998, 93-95.
7. These dianions are alkylated at the allylic position, the resulting thioesters afforded (2E,4E)-dienoates after LDA-promoted [2.3]-sigmatropic rearrangement to the 2-mercaptocarboxylic esters and S-methylation and oxidation to the sulfoxides followed by thermal dehydrosulfenylation: Tanaka, K.; Terauchi, M.; Kaji, A. Chem. Lett. 1981, 315-318.
8. (a) Caturla, F.; Nájera, C. Tetrahedron Lett. 1996, 37, 2833-2836.
9. (b) Caturla, F.; Nájera, C. Tetrahedron 1998, 54, 11255-11270.
10. 11
11. Beale, M. H.; Chen, A.; Harrison, P. A.; Willis, C. L. J. Chem. Soc., Perkin Trans. 1 1993, 3061-3064.
12. Iwagawa, T.; Amano, Y.; Hase, T.; Shiro, M. Chem. Lett. 1995, 695-696.
13. McRae, K. J.; Rizzacasa, M. A. J. Org. Chem. 1997, 62, 1196-1197.
14. Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Greé, R. S Ynlett 1994, 505-506.
15. Quinkert, G.; Becker, H.; Dürner, G. Tetrahedron Lett. 1991, 32, 7397-7400.
16. Kim, N. S.; Choi, J. R.; Cha, J. K. J. Org. Chem. 1993, 58, 7096-7099.
17. Boeckman, R. K., Jr.; Wrobleski, S. T. J. Org. Chem. 1996, 61, 7238-7239.
18. Nunu, K.; Mosset, P.; Greé, R.; Saalfrank, R. W. Angew. Chem., Int. Ed. Engl. 1988, 27, 1188-1189.
19. 7
20. For our last work on lithiated vinyl sulfones see: Caturla, F.; Nájera, C. Tetrahedron 1997, 53, 11449-11464.
21. For a recent review about synthetic applications of functionalized sulfones as carbanionic reagents see: Nájera, C.; Sansano, J. M. Recent Res. Devel. in Organic Chem. 1998, 2, 637-683.
22. 1H NMR (300 MHz).
23. 22
24. (a) Eisch, J. J.; Galle, J. E. J. Org. Chem. 1979, 44, 3279-3280.
25. (b) Nájera, C.; Yus, M. J. Org. Chem. 1989, 54, 1491-1499.
26. 7a