Tandem electrophilic and nucleophilic additions to bicyclic tert- butyldimethylsilyloxypyrrole derived from (S)-pyroglutaminol

Tetrahedron Letters

Volumn 40, Issue 13, 1999, Pages 2525-2528

  Langlois, Nicole ^a   Choudhury, Prabir K ^a  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

LACTACYSTIN; PYROGLUTAMIC ACID; PYRROLE DERIVATIVE; TERT BUTYLDIMETHYLSILYLOXYPYRROLE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033605813     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00284-1     Document Type: Article

References (21)

1. Kakeya, H.; Takahashi, I.; Okada, G.; Isono, K.; Osada, H. J. Antibiot. 1998, 48, 733-735.
2. Shiraki, R.; Sumino, A.; Tadano, K.; Ogawa, S. J. Org. Chem. 1996, 61, 2845-2852.
3. a) Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sazaki, Y. J. Antibiot. 1991, 44, 113-116.
4. b) Corey, E.J.; Li, W.; Nagamitsu, T. Angew. Chem. Int. Ed. 1998, 37, 1676-1679 and references therein.
5. Mukaiyama, T.; Hayashi, M. Chem. Lett. 1974,15-16.
6. Mukaiyama, T. Org. React. 1982, Vol. 28, 203-331.
7. Fiorenza, M.; Reginato, G.; Ricci, A.; Taddei, M. J. Org. Chem. 1984, 49, 551-553.
8. Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L. J. Org. Chem. 1992, 57, 3760-3763.
9. Rassu, G.; Casiraghi, G.; Spanu, P.; Pinna, L.; Fava, G.G.; Ferrari, M.B.; Pelosi, G. Tetrahedron: Asymm. 1992, 3, 1035-1048.
10. Casiraghi, G.; Rassu, G. Synthesis 1995, 607-626.
11. Uno, H.; Baldwin, J.E.; Russell, A.T. J. Am. Chem. Soc. 1994, 116, 2139-2140.
12. Uno, H.; Baldwin, J.E.; Churcher, I., Russell, A.T. Synlett. 1997, 390-392.
13. Baussanne, I., Royer, J. Tetrahedron Lett. 1996, 37, 1213-1216.
14. Poli, G.; Baffoni, S.C.; Giambastiani, G.; Reginato, G. Tetrahedron 1998, 54, 10403-10418.
15. Uno, H.; Mizobe, N.; Yamaoka, Y.; Ono, N. Heterocycles 1998, 48, 635-640.
16. th oct. 1998, Rouen.
17. a) Thottathil, J.K.; Moniot, J.L.; Mueller, R.H.; Wong, M.K.Y.; Kissick, T.P. J. Org. Chem. 1986, 51, 3140-3141.
18. b) Griffart-Brunet, D.; Langlois, N. Tetrahedron Lett. 1994, 35, 119-122 and references therein.
19. Chiaroni, A.; Riche, C., to be published.
20. 3 : C, 65.74; H, 5.98; N, 6.39. Found : C, 65.57; H, 6.18; N, 6.29.
21. Nagasaka, T.; Imai, T. Chem. Pharm. Bull. 1997, 45, 36-42.