Aldol Reactions of Dioxanes Derived from Tartaric Acid. A Total Synthesis of (+)-Nephrosteranic Acid

Organic Letters

Volumn 5, Issue 22, 2003, Pages 4097-4099

  Barros, M Teresa ^a   Maycock, Christopher D ^a   Ventura, M Rita ^a  

^a INSTITUTO DE TECNOLOGIA QUÍMICA E BIOLÓGICA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

DIOXANE DERIVATIVE; TARTARIC ACID DERIVATIVE;

ALDOL REACTION; ARTICLE; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

EID: 0344514156     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0354932     Document Type: Article

References (30)

1. (a) Zopf, W. Liebigs Ann. Chem. 1902, 324, 39.
2. (b) Jacobi, P. A.; Herradura, P. Tetrahedron Lett. 1996, 37, 8297.
3. (a) Sibi, M. P.; Liu, P.; Ji, J.; Hajra, S.; Chen, J.-X. J. Org. Chem. 2002, 67, 1738.
4. (b) Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628.
5. (a) Pohmakotr, M.; Harnying, W.; Tuchinda, P.; Reutrakul, V. Helv. Chim. Acta 2002, 85, 3792.
6. (b) Böhm, C.; Reiser, O. Org. Lett. 2001, 3, 1315.
7. (c) Bella, M.; Margarita, R.; Orlando, C.; Orsini, M.; Parlanti, L.; Piancatelli, G. Tetrahedron Lett. 2000, 41, 561.
8. (d) Masaki, Y.; Arasaki, H.; Itoh, A. Tetrahedron Lett. 1999, 40, 4829.
9. (e) Martín, T.; Rodríguez, C. M.; Martín, V. S. J. Org. Chem. 1996, 61, 6450.
10. (f) Mulzer, J.; Salimi, N.; Hartl, H. Tetrahedron: Asymmetry 1993, 4, 457.
11. (a) Forster, A. B.; Fitremann, J.; Renaud, P. Helv. Chim. Acta 2002, 85, 3965.
12. (b) Drioli, S.; Felluga, F.; Forzato, C.; Nitti, P.; Pitacco, G.; Valentin, E. J. Org. Chem. 1998, 63, 2385.
13. (c) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087.
14. (d) Lertvorachon, J.; Meepowpan, P.; Thebtaranonth, Y. Tetrahedron 1998, 54, 14341.
15. (e) Murta, M. M.; Azevedo, M. B. M.; Greene, A. E.; J. Org. Chem. 1993, 58, 7537.
16. (f) Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567.
17. (g) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 231.
18. (h) Sarkar, S.; Ghosh, S. Tetrahedron Lett. 1996, 37, 4809.
19. (i) Zhang, Z.; Lu, X. Tetrahedron: Asymmetry 1996, 7, 1923.
20. (j) Loh, T.-P.; Lye, P.-L.; Tetrahedron Lett. 2001, 42, 3511.
21. (k) Mawson, S. D.; Weavers, R. T. Tetrahedron 1995, 51, 11257.
22. (l) Saicic, R. N.; Zard, S. Z. Chem. Commun. 1996, 1631.
23. Gawronski, J.; Gawronska, K. Tartaric and Malic Acids in Synthesis; John Wiley & Sons: New York, 1999.
24. (a) Naef, R.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1981, 20, 1030.
25. (b) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708.
26. Evans, D. A.; Trooter, B. W.; Barrow, J. C. Tetrahedron 1997, 53, 8779.
27. (a) Barros, M. T.; Burke, A. J.; Maycock, C. D. Tetrahedron Lett. 1999, 40, 1538.
28. (b) Dixon, D. J.; Foster, A. C.; Ley, S. V.; Reynolds, D. J. J. Chem. Soc., Perkin Trans. 1 1999, 1631.
29. This assignment is based upon the structure of the principal lactonic aldol product, obtained by reaction of dienolate 10 with benzaldehyde, determined by X-ray crystallography, Lou, J. D. Ph.D. Dissertation, New University of Lisbon, Oeiras, 2001.
30. Carless, H. A. J.; Haywood, D. J. J. Chem. Soc., Chem. Commun. 1980, 980.