Asymmetric carbolithiation of 2-phenylselenofumarate derivatives: A short synthesis of (-)-roccellaric acid

Tetrahedron Letters

Volumn 41, Issue 4, 2000, Pages 561-565

  Bella, Marco ^a   Margarita, Roberto ^a   Orlando, Claudia ^a   Orsini, Monica ^a   Parlanti, Luca ^a   Piancatelli, Giovanni ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Asymmetric synthesis; Lactones; Selenium; Selenium compounds

Indexed keywords

FUMARIC ACID DERIVATIVE; ORGANOLITHIUM COMPOUND; ROCCELLARIC ACID; SELENIUM DERIVATIVE; SUCCINIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0034700794     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02119-X     Document Type: Article

References (23)

1. (a) Mahato, S. B.; Siddiqui, K. A. I.; Bhattacharya, G.; Ghosal, T. J. Nat. Prod. 1987, 50, 245.
2. (b) Mulzer, J.; Salimi, N.; Harlt, H. Tetrahedron: Asymmetry 1993, 4, 457.
3. (c) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087.
4. (d) Saicic, R. N.; Zard, S. Z. Chem. Commun. 1996, 1631.
5. (e) Jacobi, P. A.; Herradura, P. Tetrahedron Lett. 1996, 37, 8297.
6. (f) Martin, T.; Rodriguez, C. M.; Martin, V. S. J. Org. Chem. 1996, 61, 6450.
7. (g) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 274.
8. (h) Masaki, Y.; Arasaki, H.; Itoh, A. Tetrahedron Lett. 1999, 40, 4829.
9. (i) Mandal, P. K.; Roy, S. C. Tetrahedron 1999, 55, 11395.
10. (a) Schwartz, M. A.; Van Wart, H. E. Progress Med. Chem. 1992, 29, 271.
11. (b) Decicco, C. P.; Nelson, D. J.; Corbett, R. L.; Dreabit, J. C. J. Org. Chem. 1995, 60, 4782.
12. (c) Burk, M. J.; Bienewald, F.; Harris, M.; Zanotti-Gerosa, A. Angew. Chem., Int. Ed. Engl. 1998, 37, 1931 and references cited therein.
13. D'Onofrio, F.; Parlanti, L.; Piancatelli, G. Synlett 1996, 63.
14. For a review on cyclohexyl based chiral auxiliaries, see: Whitesell, J. K. Chem. Rev. 1992, 92, 953.
15. Krasik, P. Tetrahedron Lett. 1998, 39, 4223.
16. Barton, D. H. R.; Lalic, J.; Smith, G. A. Tetrahedron 1998, 54, 1725.
17. 4Se: C 69.64, H 6.68. Found C 69.34, H 6.61.
18. 1H NMR (200 MHz) signals integration.
19. Typical dialkylation procedure: the methodology outlined in Ref. 7 was followed until the addition of methyllithium (in the appropriate solvent, Table 1); the suitable electrophile (3 equiv.) and HMPA (0.1 ml) were then added and the mixture warmed to room temperature. The reaction was then quenched with methanol and diluted with ethyl acetate; usual work-up (washing with brine, extraction and drying) and silica gel chromatography afforded products 7a-c (Table 1).
20. D'Onofrio, F.; Margarita, R.; Parlanti, L.; Piancatelli, G.; Sbraga, M. Chem. Commun. 1998, 185.
21. 4Se: C 69.46, H 8.19. Found C 69.44, H 8.18.
22. Back, T. G.; Birss, V. I.; Edwards, M.; Krishna, M. V. J. Org. Chem. 1988, 53, 3815.
23. Shimada, S.; Hashimoto, J.; Saigo, K. J. Org. Chem. 1993, 58, 5226.